All The Single Ladies

Living single Archives

Match.com releases new study on singles

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Recently a research firm conducted a survey for Match.com about the behavior of singles. They surveyed more than 5,000 men and women and I have to say that I found the results to be pretty interesting. Now, let me just say that I tend to be pretty skeptical of statistics. So I know that this doesn't mean that every woman or man out there does or doesn't feel this way but never the less, I found the findings to be interesting.

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Dating shouldn't be segregated

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Yesterday I received a less than flattering comment through the contact form on my personal website. And while I am not a fan of those comments because they are a total blow to the ego that is not technically what this post is about but it's important to mention because it made me think and it's largely what has inspired this post.

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Rejection from the internet

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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I have to confess, if I go a certain number of days without receiving a message from a guy on a dating site I feel a little rejected. It's even worse if I log in and see that guys have looked at my profile but haven't sent any messages. As a side note here, I sometimes wonder if it's some sort of cruel joke that dating sites put that feature on the site. I mean, I get the benefits of it but I kind of hate it too.

So anyway, I feel rejected. And, I really hate that I feel that way and I hate even more that I am admitting it out loud because honestly the whole thing seems really silly to me. After all, can you really even call it rejection if you didn't actually hit on the guy in the first place?

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I won't give up on dating

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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This guy looks like he's done dating

Throughout my life, many people have told me that I am a very positive person. I can find something positive in almost any situation in life. And yes, I will openly admit that sometimes it's a little annoying, maybe even a little sickening but it's just the way I have always been.

Honestly, I have no idea where it comes from. Trust me, my life hasn't been all rainbows and butterflies. I have had my share of heartache, troubles, and what have you (we all have). It's just somehow I see the other side I guess. I see how things could be worse or how things will get better. No matter what happens, I see something that makes it seem like it's not the end of the world. Granted sometimes it takes me a couple of days (or years), but nevertheless I still see it.

I was reminded of this positive attitude in a conversation with a friend the other day. We were talking about dating and all of the annoying and frustrating things we have had happen to us during our million years of dating. He is tired of all the bad things that happen and all the excitement over dates/relationships that fail in the end. So his answer is to just give up. He wants to just stop dating. And he asked if I had ever thought the same thing.

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Book review: It Just Hasn't Happened Yet

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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I've mentioned before (on more than one occasion) that as a single person I feel like I am constantly explaining why I am single. Whenever someone asks me I generally say something about how I haven't met someone who I want to be non single with yet. After I say this I generally feel like this should be enough but we all know that sometimes that just isn't the case. Instead the other person feels they need to give you advice and/or diagnose why you are single.
 
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I am dateless on New Year's Eve and I am totally okay with that

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Woman at New Year's Eve party

So New Year's Eve is almost here - I've heard it's tomorrow, right? And I realized at some point this week that I won't have a date. I also realized that it didn't really bother me at all (read that as I realized that I don't really care).

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Advice for a reader: Should you give up on online dating?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Frustrated man hitting monitor screen on forehead

A little over a week ago I wrote a little advice for a reader who was curious to know if a guy was into her. Well, that same reader wrote again to ask my opinion on something else she is curious about - is online dating really worth it?

It seems as though she's had her fair share of bad dates and failed relationships with guys she has met off the internet. There was even a guy who told her that he felt there could always be someone more interesting to meet since there are so many potentials online. So even though he might meet a really awesome woman, he still feels tempted to respond when other women contact him.

It seems as though she is feeling a little beat up and wonders if there is a purpose to this whole online dating thing or if she should just give up.

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I am featured on Cupid's Pulse

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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It's no big secret that I recently turned 30. It's also no big secret that I felt pretty okay with being single on my birthday. In fact, I even wrote a whole list of reasons about why it's great to be single on your birthday. A lot of things have happened over the past few weeks and it has caused me to really think about a lot of things. Actually, for some reason, I thought about when I was 20 and how I saw my life at 30 then.

So, when the awesome folks over at Cupid's Pulse asked me to write a guest post about turning 30 and being single, I was completely thrilled (and highly flattered). Head on over there and check out my thoughts from a single 30-year-old.

Date Night Challenge Week 2: The birthday party

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

a young woman sitting on the bed and trying on lingerie

I have finished up the second week of the Date Night Challenge. My birthday was last weekend and there was a big party thrown in my honor. I also spent a lot of time with my mom before the big day because, well, I am her baby and that's what mom's like to do before their baby's big birthday. So that meant I didn't really have time for much dating and there's been a lack of awesome guys to date in my life lately.

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Ten reasons to be glad you are single on your birthday

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Today is my birthday. If you know me in any way outside of this blog you already know that because a) I talk about it non-stop on Twitter and b) you were invited to the fantastic party that my best friend, @chicagodaniel is having for me.

Young woman blowing out candles on cake

This birthday is kind of a big one and not just because I am turning 30 but because of the things that this birthday really means to me. I will talk more about that later but for the record, I do not think 30 is old in any way shape or form. In fact, there is not even a single part of me that is afraid to turn 30.

Anyway, when I met Mr. Google a while back I was very excited about him. He talked about coming to visit me and I told him he should save it for my birthday because I would need a date. Well, obviously I figured out some time ago that he was not going to be my date (thought we are actually friends now), but for a while there I still thought I would kind of like a date for my birthday. Truth be told (and I feel a little embarrassed here) but I really can't remember a time that I haven't been single on my birthday.

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Paid dating sites vs. free dating sites

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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This guy looks really serious. I wonder which dating site he is browsing.

A couple of weeks ago I had the opportunity to meet Sam Yagan, the CEO of OkCupid for breakfast. We had a pretty fantastic talk about dating, specifically online dating. Seems logical right? I mean what else would the CEO of an awesome dating site and a dating blogger talk about?

We talked a lot about OkCupid and other dating sites and he asked some of the things I like about OkCupid. Aside from the fact that I seem to find some amazing blogging fodder from the site (aka the DTF guy and the guy who offered me free pie), I also said that I like that there is an instant messaging service because I feel like you can weed out creepers without giving them personal information.

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A date shouldn't be treated like a job interview

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Businessman in Meeting

A couple of days ago a reader left an awesome comment on my blog which really made me think. The comment mentioned how a lot of women treat a first date like a job interview which is something that I feel is true. It's something that I will openly admit that I have been guilty of in the past.

Honestly, I wish we could get past this idea that you have to be completely perfect on a date. When I first moved to Chicago, I spent a lot of time dating like that. I have to tell you it honestly wasn't any fun. I mean, one time when I met a guy for drinks the first thing that flew out of my mouth was a comment about how I sweat when I am nervous. Clearly that's not hot in anyway but I also don't think that sort of thing is really that big of a deal. And I am pretty sure that I don't want to date a guy that worries about something silly like that.

I used to beat myself up about things like. And as I was getting ready to meet a new guy I would always go through the list of things that I did wrong on my previous dates. It was exhausting.

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The BreakUP Club

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Break ups suck. I honestly tried to think of a really clever and creative way to word that, but let's face it there isn't one. Even if you see it coming. Even if you are the person who is ending the relationship. Even if you know there is not a shot at the relationship working. It doesn't matter, a break up is no fun at all.

That's why I am really excited to share a new project that Tristan Coopersmith (one of my favorite relationship coaches) is starting. The project is called the BreakUP Club and the idea is to turn a break up into something positive. It's a place where women can come together to get over a crappy break up in a very positive way.

Anyone who knows me can attest that I am far too positive for my own good so I am definitely a fan of this. Actually I am a little jealous I didn't think of it myself.

The BreakUP Club is offering a free workshop if you are in Los Angeles. Here are the details:

BreakUP Club Introductory Event
October 12, 2010
7:00pm-8:30pm
Blank Spaces
5405 Wilshire Blvd (b/w La Brea Blvd & Hauser Blvd)
Los Angeles, CA 90036

The first in-person meeting should not take place at my apartment

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Man knocking on door, (Mid section)

I was chatting with a guy from OkCupid the other day. We had talked for a while and agreed to meet over the weekend. He was about to get offline when he told me that he needed a time and an address for our meeting. I asked what he wanted to do and he responded that he thought he would come see me (he lives in the burbs) which I found out meant he wanted to come to my place.

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Does it even matter if there is someone out there for everyone?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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"Dear God, please bring me a boyfriend this year"

I was having a conversation with a friend the other day about my frustrations with dating. It's been quite a run with me and this whole dating thing. Frankly I just get a little annoyed when everything seems to end up the exact same way. And while it's something I know I could never give up on (it's just not me to really give up on much of anything), I still have to say that sometimes I wonder if it's really getting me anywhere.

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All The Single Ladies is invading New York City

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

I know I have slacked a little lately on this whole blogging thing but this has been one crazy (but very great) summer. The sad part is that I will be signing off, but only for a week because I am taking a trip. That's right folks, All The Single Ladies (or I guess technically the author of All The Single Ladies) is invading New York City.

I cannot even begin to describe how excited I am about this trip. And that's not just because it's been far too long since I have taken a trip or because it's New York City. Wait, who am I kidding? I am stoked for those reasons but also because I am getting the chance to meet a lot of truly fantastic people there and see a few friends I haven't seen in a while.

I will be back next weekend with a fun new post. I might have a few tales of my adventures while I was away to share and I will even have a really fantastic guest post. In the meantime, check out a few pictures from the last trip I took there. And wish me luck.

Gallery sneak peek (9 images):

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Does your single status really say anything about who you are?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

 

 

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I know I have written about why I am single many times before but it kind of seems like it's a subject that a person can go on and on about. There are so many ways to look at it and there are always new thoughts that come up. Let's face it, when you are single you almost always run into someone who wants you to have some clear cut reason for it.

Honestly the question annoys me because I don't understand why it always seems to come up. Why do people need a reason? It almost seems like people always want to diagnose that whole single thing - I mean there must be a reason for it, right? Never in my life have I ever heard anyone ask a person why they are in a relationship. So what's the deal with asking single people? I mean really, it's not that weird to be single is it?

One thing that really bothers me is when I start talking to a new guy and that is one of the first questions that flies out of his mouth. I mean forget what your favorite movie is or your hobbies. No, instead they want to know why I am single.

I can admit that sometimes that question spawns interesting conversations, like when a guy shares stories with me about his crazy ex-girlfriends. But more often than not I feel that question is used for some sort of judgment. It's almost as if people think the reasoning behind your single status will explain everything about you and will also somehow determine if you are relationship material or not.

It's like that question - when was your last relationship - which, coincidentally I am equally annoyed by. Does it really honestly matter when it was? Actually, I have to tell you I am more afraid of the person that tells me their last relationship was a month ago than the person that says 10 years ago.

Honestly, I have a couple of thoughts on all of this. First of all, you don't really want to know the real reason why I am single. I mean, let's be honest here if I have decided to stay single because I wanted to have sex with half the city, do you really (I mean really) want to know that?

What you really want is some kind of confirmation that I am not some psychotic bitch or assurance that I want a serious relationship. Which brings me to my second point - if you really want to know if I am relationship material then try dating me.

I have to tell you, if I am some crazy psycho who slashed my ex-boyfriends tires, I am surely not going to tell you that's why I am single. Likewise, just because I haven't been in a relationship for the better part of the past decade doesn't necessarily mean I am not relationship material. I mean maybe I have made some mistakes in my past and took time to learn from them. It also be that I wasn't ready for a relationship before and now I am.

Now sure, I am not going to deny that there are probably cases out there where the answers to these questions were spot on about what a person was really like and there are obviously some pretty sketchy reasons for a person's single status. But I will argue that it's not always the case. The reason for being single or the length of time that a person has been single doesn't necessarily tell you anything about a person. Plus it's really easy to sugar coat things (or flat out lie).

The fact of the matter is that people will tell you who they are if you really listen so how about just taking a little time (or you know, at least a couple of dates) and get to know them a little. That to me seems like such a much better and it greatly increases your chances of actually knowing what a person is like. 

 

 

 

 

 

 

 

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It's called having sexual confidence

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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The other day, I was talking to a friend that I have known for a while. He doesn't live in Chicago so really we mostly trade e-mails back and forth. Occasionally his e-mails involve something to do with my blog since he reads it fairly regularly.

Anyway, we were discussing how some guys choose to approach me when they are "hitting" on me. He advised that I should be aware of my confidence and sexual aura (actually he flat out said to be careful how I use it). And also talked about how I blog about sex so maybe some guys get a certain idea about me.

I am not so sure how I feel about that. Actually, I entertained his ideas for a few moments and then thought to myself are you kidding me?

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In defense of the nice guy

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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For some reason I have been thinking about this whole nice guy thing lately. It could be that Mr. Google
appears to be a pretty freaking nice guy. But then again it could just be that I randomly think about things and then over analyze them to death. After all, that is what I do best as a writer/blogger.

When I was younger, I was way too into bad boys. I mean I was that girl that broke up with guys because they were too nice and then started dating the bad boys. I dated a guy that stole my parents' credit card, there was also a guy that didn't graduate high school and was heavily involved with some highly suspicious entrepreneurs (if you catch my drift). Half the guys I dated didn't have a driver's license because they were in trouble with the law in some fashion.

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When the ex comes back around, Part 1

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Man outside window

A couple of nights ago, I was enjoying a few moments of couch time when I received a text. I looked at my phone to see who it was from and I was a little shocked. The text read "hey what's up it's Mr. BST." It took a few minutes to actually sink in and, honestly, I'm not sure if I can pinpoint what I felt at that very moment. Anger. Frustration. Sadness. Curiosity. Far too many emotions.

Mr. BST was my first love. I guess you could call him my ex though I have to use that term pretty loosely here because I'm not really sure what he is or ever was. But the important thing to know here is that somewhere in whatever we were (or weren't) doing we fell in love. Utterly, madly, hopelessly in love.

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Why can't we be friends?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Friendship Day with children and dog  

A thought occurred to me the other day - why do I seem to find so many guys that are opposed to being friends? I have had many conversations with guys, both from internet dating sites and just in general, and more often than not I hear things like "I'm not looking to make friends" or "I have enough friends already."

I'm not really even sure if I understand the phrase - I have enough friends. How is that really even possible? Are you really so popular that you have no room left in your life for another friend? I mean, you really can't even entertain the idea at all?

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A good date happens (once in a while)

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Man and woman laughing

I feel like I never really write about the good stuff that happens in dating. It could be that not enough good stuff actually happens (to me anyway) but I really hate saying that. I don't want to be the cynical woman that thinks that. The truth is, life (and dating) is not all rainbows and butterflies, bad things happen. Plus I feel like I have so many stories to share about my misadventures with guys that sometimes the good just escapes me.

Anyhow, I made a vow to myself that the next time something good happened I'd blog about it. After all, it's only fair and I like to play fair. Well, I am sure that you have guessed by now that something good has happened and it might seem small but I believe you should always keep promises.

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Sometimes I am busy (Part 2) - I don't respond to threats

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

 

Man with laptop sitting on stool

Dating is frustrating (I am pretty sure I have said that before) and more often then not things don't go the way you want them to. Sometimes I think Saturday would be a great date night but the guy isn't available until Sunday. Sometimes I like guys that have no interest in me at all. And more often than I care to admit, I want what I can't have. We've all been there, but it's life and you have to deal with because let's face it there isn't really anything else to do about it.

I came back to the city earlier this week. Actually I came back a day later than I thought because there was a little mishap with the train schedule. Needless to say I was tired, a little cranky, and was really just ready to be home. Of course Mr. Doesn't Understand That I am busy that I talked about in my previous post started in with his spiel about how he really wants to meet me and so on.

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Sometimes I am busy (Part 1)

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Shadow of annoyed woman at computer

The fact that I tend to be a pretty busy girl is pretty well known to anyone who knows me. This is not a fact that I hide or sugar coat from guys when I first meet them. There are times when I don't have that much on my plate and other times when my plate is full everyday. I've always thought this is pretty normal for the life of a single woman in the city.

Now, before I go any further, let me make it clear that I genuinely try to make time for dating. And if I meet a guy I want to seriously date I will definitely make time for him in my life as well. But do I really feel the need to keep a few nights open just in case I get a date? Probably not.

With that said, obviously this can be a problem when I am trying to set up a first date with someone. As hard as I try, sometimes it's just not possible to set up something for a few days and in some cases it might have to even wait a week. I don't say that to come across as some kind of superficial bitch or to imply that my life is anymore important than anyone else's because I definitely don't feel that way. All I genuinely ask for is a little patience when this happens, especially when I am being upfront about it and when I would do the same thing if the situation was reversed.

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There is an exception to everything

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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I have always been the woman that can totally separate sex from feelings. I understand that people you are having sex with don't always care about you and that you don't always have sex with people you care about. Let's all be honest here, no matter how bad it might sound, sometimes people are just there for simple pleasure. It might be wonderfully blissful mind blowing pleasure, but never the less, it's just pleasure. I also understand that sometimes the line between sex and feelings can get a little blurry which is something that has caused me a little trouble in the past.

There was once a guy that I had this insane crush on but it became evident to me that the feeling was not mutual so I pretty much closed the door on the idea of dating him. As we spent more time together, we managed to become awesome friends. Until one night we engaged in a pretty heavy make out session that turned into two years of fooling around during which I took his virginity.

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Just because I don't want to sext doesn't mean I am a prude

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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It's really no secret that I meet guys off the internet, therefore it's not all that shocking that I also give one my number from time to time. Honestly, I have to say that I am not overly excited when I give a guy my number only to have him text me in return. Call me crazy, but I think if you ask for my phone number then you should just pick up the phone and actually call me. However, it's not really a total deal breaker so I tend to just let it slide.

Texting with a new guy generally starts out pretty simple with questions about my day or what I am doing that weekend and so on. This is all fine and dandy to me. However, sometimes the personal questions start to slowly creep in and he's all interested in my favorite position and the craziest place I have had sex. Then, the conversation totally takes an even bigger turn and next thing you know he's talking about how horny he is and asking if I would like to help him out. Followed by a very through and explicit description of all the things he wants to do to me. And all I am left thinking is how did this happen? How did we get from talking about going to see my sister to you asking if I'd like to see a picture of your penis?

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Some guys should be banned from sending me messages online

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Man typing on laptop

I haven't really given my profile on Plenty of Fish a whole lot of attention lately. Honestly, I am not sure if I have this fantastically brilliant reason as to why that is the case, that just seems to be the way it's been happening lately.

So it seems only logical that I was a little surprised the other day when I received an e-mail alert that someone had sent me a message on there. I tend to get a little excited when someone sends me a message from an internet dating site. That's totally normal right? I guess it's just the excitement of possibilities and, I mean, let's face it, who doesn't like the idea of someone thinking they are attractive?

At any rate, I logged on to read the message and was even more surprised because I immediately recognized the guy's picture. He is someone that I met and went on a couple of dates with when I first moved to Chicago. I can't recall the specific details about our encounter, but I do remember being a little interested in him. That is, until he fell off the planet only to resurface a few months later claiming he really liked me and made a huge mistake but only to fall off the planet once again.

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To fling or not to fling (with a 20-year-old)

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Young Man Sleeping in Bed

I've bitched mentioned before that I seem to attract a lot of 20 to 22-year-olds on OkCupid. If you read my blog, you know that I've encountered my share of younger men during my time as a single woman and it's definitely never been a secret that I am not a huge fan.

Honestly, I would like to say that I have some grand explanation for it but the truth is that things between me and the younger fellas just don't tend to work all that well. Nevertheless, I can't deny that some of these younger dudes are super hot which makes flirting with them a whole lot of fun (that is up until the point when they start annoying the crap out of me). And I should also confess that I find myself salivating far more than any grown woman should ever admit, over many guys this age during my commute to and from work each day on the bus (if you follow me on Twitter, you have seen my highly inappropriate tweets on this subject).

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So why be in a relationship if you're happy being single?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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The other day I was having that whole "get to know you" conversation with a new guy. We chatted about various things and the subject of writing came up which of course led to the topic of this blog. Then, somehow, I was faced with the question about why I would want a relationship when I was content with my status as a single woman.

Essentially I guess the guy was not expecting to find out I write about dating and single life. Then of course he felt I wasn't a woman who would really be interested in a relationship since that could alter the subject of my blog. I told him that I am definitely open in having a relationship and I will handle things as they come. This seemed to settle him but then he listened to me on the radio. Apparently something I said made it very obvious to him that I was happy being single and it made him wonder why I would want to change anything if I was happy.

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What will it take for men to go to singles events?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Today's blog is a little something different, but that is because I am legitimately curious about something. So I am hoping all the single guys out there can help me out. Why is it that so few single guys go to singles events?

Group of men
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I'm bored so do you want to go out?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Bored man waiting at table in restaurant

We've established that some guys need to learn what a date really is (and also a better place to meet women off the internet). Well, I kind of feel like we need to go into this whole asking a girl out on a date thing. I am just going to get straight to the point here, the words "I'm bored" should never be followed by "would you like to meet" (or any other derivative of that).

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Sitting on my couch is not a date

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Destroyed couch

I've had a epiphany this week. Actually, back up for a second. Technically I have been thinking about this for a while, I just feel like it was fully confirmed this week. If you read my blog, you know that I am pretty open minded when it comes to dating and by no means am I a prissy princessy kind of girl. I have to be honest here though guys, sitting on my couch (or your couch) is not a date. Really, it's not.

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Guest post: So...do you want my phone number or what?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

It's time for another guy to guest blog on dating rules. This time we have a post from Dennis Frymire about that whole "you have to wait three days to call a girl" rule.

Woman offering piece of paper with her phone number
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Need to pretend to be committed? There's a ring for that

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

For anyone who is keeping count, we have established that I am not obsessed with marriage but that I want to fall in love. We have also established that I don't think a woman is ever really unmarried but that she can be single at any age. It would only seem fitting that last night while watching MTV, I would discover that someone has decided to make an entire business out of helping women pretend to be committed.

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Guest post: The one night stand

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

The past couple of weeks I have had some of my favorite male bloggers talk about dating rules. Well this week Matt is throwing a different spin into the mix with some talk about the one night stand. Matt is the editor of LoveintheDumps.com, a dating/relationship comedy collective, and the upcoming Impersonals, a dating site parody.

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Dating lessons: Chicago is too small and I attract crazies

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Funny Facial Expression

For some reason, over the past few weeks, Fridays have seemed to be my day of reflection. I am not really sure why that is but I will go with it. This week I have learned two things. First, Chicago might be a rather big city but it's much smaller than you think. Second, if there is a crazy guy within a 50 mile radius he will find me and want to date me.

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When does a woman go from being single to unmarried?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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A few days ago I posted about how I am not looking to just get married but to also fall in love. It was a post that was very personal to me and I felt good about it. Well apparently from an article I have seen bouncing around, I need to watch myself because I only have about a decade or so before I move from being single to being unmarried. Honestly, I wasn't even aware that there was a time that women went from being unmarried to single. Clearly you learn something new everyday,

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Guest post: Should a woman ask a man out?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Last week I talked about how I have invited some of my favorite bloggers to talk about dating rules. It's only fair that we let the fellas out there weigh in right? Well this week my friend Jack From Brooklyn, tells his thoughts about the age old question: should a woman ask a man out?

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Things I'm learning as I go

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Metal type spelling blog

This week has been an especially challenging one - both for me personally and amongst the people I know in bloggersphere. (I realize that I don't normally write about this sort of thing, but it's what I am feeling so I am just going to go with it). Anyone that knows me will tell you that I am a really positive person. I believe that everything happens for a reason and that there is almost always a silver lining. Needless to say, I have learned a lot over the past week.

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The 22-year-old approach to picking up an older woman

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Student Asleep During Lecture

Will someone please tell me what the deal is with 22-year-old guys? Seriously, their approach to picking up women (mainly older women) just flat out sucks.

Anyone who knows me will tell you that I am not overly fond of guys that are younger than I am (actually I am not overly fond of guys my age either). I tend to be into those that are more in the 32 to 35 age range - with an even bigger preference for those that are even older. Honestly I have no idea why this is; it's just how I have always been. Clearly I would love to say it's because I have better luck with older guys, but I am not really sure if I can say that.

Point being that there is a pretty big age difference between 22 and 32, especially in man years. So yes, I get that it's an age thing. Though, it's something that seems to be a trend which makes me wonder. And I mean, even if it is a 22-year-old is it too hard to ask for a little respect here?

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It's not giving up it's just moving on

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Man sitting in back of van holding cup, low section

Anyone who knows me will tell you I am a pretty impatient person, I always have been. I am the type of person who likes to get things done and I always go after what I want. It's part of what brought me to the city - I need the hustle, the noise and all it's craziness. These are things that just seem natural to me, it's who I am. Sometimes I wonder, though, if it makes me give up too easily.

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Standards vs. rules in dating

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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My friends sometimes think I am too open-minded; I often think they are crazy. I have always been a person who doesn't like to play by the rules, just ask my mother and my sister. It seems so easy to miss out on life when you are so busy worrying about the list of things you should be doing. Though, I have been noticing lately that this can be a problem with it comes to dating. And it's important to remember there is a huge difference between standards and rules.

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Using a crutch for sex is probably not your best laid plan

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Man with crutch

We all have our staples when it comes to sex. A lot of women tend to have underwear or something that makes them feel sexy. Men sometimes do a couple of push ups when you are in the bathroom so they feel a little hotter. Those things I get. However, I have never in my life met a man that uses his apartment (or anything in it) as a crutch for sex.

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Please meet me in person before inviting me into your bed

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

man sits on the bed in de sleepingroom

A little while ago a friend wanted to fix me up with another friend and all the guy could talk about was having me over to his place. And he wasn't talking about cooking me a little dinner and playing some trivia on the Wii (read that as he just wanted to have sex with me). I guess he's had an issue with some women that are just too attached after the first date. So he's not to keen on the whole date thing. Apparently now he is punishing all women, including me.

This is not the first time I have been in this kind of situation.

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Sometimes dating different types isn't really all that different

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Everyone knows by now that I am a huge advocate for dating all different types of guys. I genuinely feel that when you only date certain types of guys that you just limit yourself way too much and might miss out on something really fantastic.

Whenever a guy asks me what my type is I always answer that I don't have one because honestly I am not sure if I do. I tend to not get caught up in labels and honestly I want to focus on getting to know a person rather than worrying about what "type" he is. However, I have started to notice something lately. Even though I date a variety of guys they all seem to have one thing in common with each other - they're unavailable.

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Online dating messages gone bad: A date and free pie?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Oh I love internet dating and all the messages that people send.

Of course that means I have one to share. Though, this time the message did not offend me nor was I completely confused about what the guy is taking about. Nevertheless, it is a fine example of an internet dating message gone really bad.

close-up of a slice of pie with ice cream and a cherry garnish
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Recap of the All The Single Ladies and Sex and the Windy City Singles Soiree

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Well, the All The Single Ladies and Sex and the Windy City event was this past Saturday and I have to say it was a blast. Everyone drank, played games and mingled.

Thank you to everyone who came out to the event and to everyone who helped make the event possible.

And, of course, thank you again to all of our fantastic sponsors.

Gallery sneak peek (17 images):

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Let's be exclusive friends

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Man Leaving an Apartment Building

A little while ago, I had the most interesting conversation with a guy on OKCupid. Everyone knows that interesting actually means to weird or puzzling which generally translates to blogging. So here we are.

It went a little something like this (I didn't change this conversation and I am really sorry it's so long, but as you will see I needed to include it all):

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Apparently even crazy comes in threes

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Hand making three sign

Lately, I have been thinking a lot about third dates. I have noticed a pattern with the guys I date. And then I had a conversation earlier with a woman I know about how relationship milestones come in threes.

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I think it's time to define relationships

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Young couple lying in bed

Relationships are tricky and generally, what works for one person doesn't necessarily work for another. Let's face it, dating will never be that cut and dry. Which is why I am a firm believer that people should define their own relationships. There are, however, certain core ideas that make up different kinds of relationships that are usually the same across the board. After many conversations with various people I have met, I have realized that many people really don't know the difference between these types of relationships

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Breaking up is hard to do, but just do it already

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Sad Woman Turning Away from Man

I had a conversation with a friend the other day who was about to end things with a girl he was seeing. He said he wasn't really sure how to do it and that the whole situation was making him feel like a total ass. Which we all know really made me think and thinking leads to writing and here we are.

So, tell me something here. Why is it that guys feel like such an ass when breaking up with a woman?

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Help! I'm on a disaster date

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Couple yelling at each other

Shows on MTV are quite entertaining and since I was sick today, I caught a whole marathon of Disaster Date. In case you don't know, the idea behind the show is exactly what the title suggests. People hook their friends up on blind dates who do everything on their list of dating don'ts. The date and everyone else involved are all actors. Then the friends are given one dollar for every minute they stay on the date, the goal being for the date to last an hour.

 
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Who cares who asks who out on a date

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Dating is already confusing enough and this whole idea of who should ask who out honestly just makes it worse. I continually read about it in every dating book that I pick up. The consensus essentially is that if you are a woman, you should never ask a guy out. Sure, you can hint around to it and try to convince a guy to ask you out. However, you should never actually ask him out.

This is a concept that I honestly don't understand. I mean did I miss something here, it is 2010 right? With everything else that is evolving in the world, why hasn't this?

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Guest post: Learning happiness

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

 

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A couple of weeks ago I had a guest blogger named Samantha Karlin who wrote about how to write an online dating profile.

I have invited her back, this time to talk about how to be happy and content. Even more importantly, how to have a great outlook on things even if living the single life gets you down.

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Don't act like you don't care about sex on the first date

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Sex on the first date. This really isn't breaking news here. I mean, there is really nothing new about this dilemma. While obviously I don't know for sure, I am pretty sure it's been around since the whole concept of dating was invented.

Every dating book that I have ever read that talks about sex on the first date says it's a bad idea. Many guys I have talked to/dated say it's a bad idea. I would say it seems as though the consensus is that it's a bad idea.

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30 dates in 30 days: The 30 Dates Project

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Let me introduce you to Elizabeth, Joe, Marisa, Laura and Sarah. Singles who are out there in the dating scene. Singles who are on a mission to find (and go on) 30 dates in 30 days.

Wait, what?

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Have you ever double booked?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Lately, I have heard a lot about double booking dates. The subject came up on a few shows and movies that I have watched lately. Then the other day I saw a couple of posts about it on Twitter.

If you don't know what double booking means, essentially it's having two dates back to back in one day. Now, I have to say that I personally have never double booked. Though I can't say it's because I think it's wrong, it's just simply because I have never found myself in that situation. Generally if a guy asks me out and I already have a date I tell him that I am busy and try to plan something for another day.

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Online dating faceoff from Mashable

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Every week Mashable puts two similar things together for a faceoff to see which one people think is better. This week's match up is between plentyoffish.com and match.com in honor of the super romantic holiday that is approaching us.

In case you don't already know, the two sites are the biggest in online dating. Match.com being a paid site while plentyoffish.com is a free site.

So which one is better? Click here to find out more and throw your two cents in. Voting ends at 12:00 p.m. PT on Valentine's Day.

Also, let me just add that if you have checked out either of these sites, I strongly recommend it. They are both great sites to meet some interesting people (thanks Ms. Obvious. But no, really you should).

 

Speed dating? No wait, speed hating

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

If you've ever been speed dating, you know that it can be a little intense. Let's face it, getting three minutes to shine so someone will check the little box that says "yes" next to your name isn't exactly the ideal kind of first date. Though I guess compared to some of my dates that really isn't all that bad and at least you don't have to come up with some clever get away plan if the date goes horribly wrong.
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Love Bites: Anti-Valentine's Day events in Chicago

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Whoever said that the people that like Valentine's Day are the only one's that get to go out and have fun? If you feel ignoring the icky love stuff and doing a little anti-Valentine's Day celebrating then Chicago has you covered. Check out one of these fantastic events this weekend.
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10 reasons to be glad you're single on Valentine's Day

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Even if you are completely happy and confident with your single status, there is one day that makes you suddenly aware of the fact that you don't have a significant other. I have always felt that Valentine's Day is about having love and this could be any kind of love, including the love you felt for the guy that gave you your bagel at Einstein's.

No matter how you feel about the holiday, here are 10 reasons it's great to be single when the day rolls around.

Gallery sneak peek (10 images):

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Five traits I never knew were deal breakers

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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A new book has surfaced which could make quite a few single women rethink their dating strategy. Marry Him: The Case for Settling for Mr. Good Enough by Lori Gottlieb hit store shelves yesterday and it's actually causing quite a controversy. The book is about exactly what the title suggests - women settling for "Mr. Good Enough" instead of holding out for "Mr. Perfectly Right."

I will admit that, as a single woman, I find the title of the book really hard to swallow. Honestly I think if I was a man I might have a few issues with it too. Since I haven't read the book I feel it's a little tacky and unfair to really critique it in anyway.

Though, my curiosity has been piqued, which of course led me to do a little research on the author and some of her ideas.

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Pre-Valentine's Day events for singles

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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While technically you don't need a date to have fun on Valentine's Day, having a date any day of the week never really hurts. So if you want a chance to meet some other singles before the love fest arrives, check out these pre-Valentine's Day events.

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Online dating messages gone bad: You look like a girl who is DTF

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Apparently there is a shirt that actually says it. This little shirt right here can be found at bufftees.com

Once again, I have yet another message to share from OkCupid to continue with my series Online Dating Messages Gone Bad.

This is actually a pretty short but not so very sweet message. As always I didn't change the message in anyway, just omitted any personal information. This is what was in my inbox:

Subject line: dtf

Message: you look like a girl who is dtf

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Should I keep seeing him?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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I received an email the other day from a woman I know who is having a little dilemma with a guy she's recently started seeing. Here is the gist:

She met a guy through mutual friends and they immediately hit it off. A few days later they met for a quick drink and then that weekend they had their first "formal" date. Though he ended the date with a kiss she seems a little thrown by him. First, he asked her out via text, which is a huge no no in her book. Second, he didn't offer to pay for any of the date at all. Essentially she isn't sure if she should keep seeing him or not.

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First date etiquette: How to handle public transportation

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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© Jeremy Atherton, 2006

One reader "Bald Chi Guy" (whose name I believe may actually be Dennis) mentioned the other day that he would like to know the etiquette for ending a date when you are using public transportation. Ah yes, yet another thing first daters have to be confused about.

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The non-drinking guy: Deal breaker or not?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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One of my fellow bloggers Sex and the Windy City, brought up a really interesting point the other day when I wrote about drinking on the first date. She asked "what if you like to drink and your date is a non-drinker, is that a deal breaker?"

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Drinking on the first date (when your date isn't drinking)

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Drunk Girl.jpg

When I wrote for examiner.com, one of my dating don'ts involved the subject of who should pay on a date. More specifically how you shouldn't be rude about paying for a date. Let's face it first date etiquette can be a little tricky especially when it comes to who should pay. It's an age old question and honestly I am not sure if there is a right or wrong answer, it's just something you have to deal with.

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Online dating messages gone bad: Hi hotty, I want be with you all day and night

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Continuing with my series called Online Dating Messages Gone Bad, I thought I would share this one.

The other day I was on OkCupid checking messages when I received an instant message. For those of you that don't know, OkCupid has its own instant messaging service so you can chat with other members. This is something I actually kind of like because it makes sending a message to a total stranger a little bit easier.

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Never trust a guy who never calls you over the weekend

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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It is my firm belief that if a guy only calls you on a Monday night that he's probably not worth your time. Now, I don't really mean Monday literally here, but more metaphorically. You know the guy that I am talking about. He calls you on Monday to see what you are doing and wants to do something that night, never making any sort of plans with you. Sometimes the calls continue through Tuesday or Wednesday but then they stop. Then all of a sudden he resurfaces as the next Monday rolls around.

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I want to be on Tough Love

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

I know, I know. Another trashy television show. Really though, this one is extremely entertaining (aside from the trashy stuff). And honestly, I kind of think people can actually learn a couple of things about dating from it.

If you don't know the idea behind the show. Steve Ward, a professional matchmaker, takes relationship challenged women and makes them into A+ daters. There's the woman that's obsessed with getting married, the gold digger and the woman with the body issues just to name a few. Steve pairs them up with dates and gives them the do's and don't of dating along the way. Of course he throws a few curve balls at them here and there, it is television after all.

Now, I must say that I don't really perceive myself as "relationship challenged." Though I mean I am almost 30 and still single so a little advice doesn't ever hurt right? Honestly, I really just want to hear what Steve has to say about me and my dating style. And, he seems to be pretty good at fixing these women up with some pretty great guys. Great dates definitely never hurt either.

I like Steve, I even think maybe we could be friends. Plus he's one matchmaker guy that I actually agree with most of the time. Of course I am also a little curious about how many times he would make me cry and how many times I would end up in the hot seat. For those of you that don't watch the show, the "hot seat" is for the woman who has done the worst for that day's events.

So who will nominate me? And Steve, if you are reading please pick me for the next season of Tough Love.

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If he doesn't call to get his hat back then he's just not that into you

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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This is not the actual hat. I am not sure if I would call a woman to get this hat back either.

I feel like I am a pretty smart woman when it comes to knowing if a guy isn't into me or not. You go on a great date, its been a couple of weeks and you haven't heard from him. Pretty clear he is not interested right? Maybe you send him a text or call him and he doesn't respond. Again, pretty clear he is not interested. Generally I feel this is pretty straight forward and I am not the woman who makes excuses about why he didn't call and so on.

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How to end the first date: The worst advice ever

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Dating books are a lot of fun. Generally I like to read them out of curiosity, I always wonder what other people have to say about dating and being single. Plus a little advice never hurts a girl right? Lately I have been reading this book called Why Hasn't He Called. Actually, I would like to call it The Cookie Cutter's Guide to Getting the Cookie Cutter Guy since I feel like that title is far more fitting for the book.

As a side note here, I feel like I should sort of defend the corny title here. Actually, I read the reviews on Amazon.com and that is what hooked me. Honestly, I couldn't believe that a book would actually recommend some of the things the reviews said so I had to see to myself. I am almost done with the book and I have to say the reviews didn't disappoint me. They weren't lying at all. This book gives some of the most absurd advice that I have ever heard.

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Is this a desperate man?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

I had a casual e-mail conversation with a guy from Plenty of Fish and we ended up on the subject of being desperate. Actually I think it's fair to say we kind of started a debate about it because never in my life had I heard the things he was saying.

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The Single Mingle Show at Spy Bar

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Something new is coming to the single nightlife in Chicago. The Single Mingle Show is an interactive dating show similar to the dating game. It is Chicago's only live dating show. What could be more fun then a night out in the city mixed with a game show?

The debut of the show will be on January 23 at 6:00 PM and will be hosted at Spy Bar.

To find more information about the show and how to apply to be a contestant click here.

I really appreciate that you like me

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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A little while ago I sort of put my feelings out there for a guy by telling him that I was interested in him. His response? "I really appreciate that." Ouch thanks douche bag really. I mean generally I am not an advocate for that whole no response thing, but clearly in this case I would have rather had that. If you can't be honest then why even bother? Why are guys such wussies when it comes to telling a woman they are just not that into her?

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My niece has given up hope I will ever get married

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Kids are fantastic. I mean there is nothing like a kid's perspective on the world. They tell it like it is with brutal honesty. Plus, they rock at giving compliments to make your world a little better when you feel like it just plain sucks.
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Frank the Entertainer is trying to find love

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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One of Frank's super classy moments. Photo courtesy of VHI

In case you didn't know, I kind of have a thing for trashy television. Mainly that in the trashy reality television show category. Last night, I caught the premiere of Frank the Entertainer in A Basement Affair on VH1. Obviously the show did not disappoint me. I do have one question though. Why in the world are these women competing for a man who lives in his parent's basement?

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Confident being a single lady? The Ah Ring is for you

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

If you are a woman who is confident with her status as a single lady, then you definitely need to check out the Ah Ring. Created by Ruta Fox, it is the first and only ring diamond ring created just for single women.

The Ah Ring stands for availably and happy, which is pretty clever in my opinion. It was created as a way for single women to show the world they are available and proud of it, which is of course is equally clever in my opinion.

As Ruta put it in an e-mail to me:

I figured married and engaged women had their ring, why not one for single women? It's about feeling good when you are single, and empowered, joyful and confident.

To find out more about the Ah Ring and how you can purchase one of your own, check out the website here.

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Where are all the hotties at?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Limelife.com recently put out lists on where to find all the hot single men and women in America. The information came from the U.S. Census and the 2009 Men's Fitness rankings of the top fit cities. According to the list, most of the fit and single men are in Salt Lake City, Utah while the fit and single women are in Boston, Massachusetts. Chicago seems to be in the middle with a decent blend of both fit single men and women.

Now, I have to say that I originally found this on AOL where I found the author to be a little annoying. I mean this is tragic really. If all the fit (and super attractive) people are on opposite sides of the country how in the world are they supposed to get together?

Here's the thing though. How in the world does being fit suddenly make you a hot eligible single? Even more then that, how does being fit make you automatically compatible with another person that's fit? I mean who knew that was the secret to eternal happiness really.

I don't think you can really go as far as to say that this is where all of the hot singles are. After all, I would like to think there is a little more to being hot then just being fit. There is right? Yes, I can value a guy who takes care of himself. And if a guy is the sort of person who works out seven days a week and has no body fat then kudos to him, really. To each his own is what I always say.

Clearly I understand that whole physical attraction thing and think it is definitely important. There are physical characteristics you like and some you don't. Likewise, there are people that you are attracted to and people that you aren't. However, a hot body is not the only attractive physical quality about a person. Simply having a hot body does not automatically equal attraction and I would say some people would still be likely to pass (at least on anything more then just a night).

As for relationship compatibility, I would really like to think that we are not that superficial. Now, I can understand that being fit is a lifestyle preference and obviously it's something that you want to have in common with your mate. I mean dating a couch potato when you are fit is like an environmentalist dating someone that drives a Hummer and throws trash all over the place. Yeah, definitely not compatible and there is no argument with that at all. On the other hand, can you definitely say that just because a person shares being fit with you (or any other lifestyle preference for that matter) that you are automatically compatible? I think not.

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Where is this relationship going?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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One of my fellow bloggers, Sex and the Windy City recently wrote about defining a relationship. Which of course lead me to think about it as well. We've already established that this whole dating thing can be really confusing - that's kind of a no-brainer. And let's face it, the idea of where it's going and if the two of you are on the same page can sometimes be the most confusing.

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Deal breakers in dating: The bad first move

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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When you are dating guys over say the age of 25, it is inevitable that they have been on a date or two. Which also makes it pretty inevitable that they have kissed a girl and probably done all that sexual stuff too. Now, I am sure there is a 29-year-old out there somewhere that hasn't really been on a date with a woman. However, most of them have been around the block one or twice (some of them more times then they care to admit).

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The 26-year-old effect

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

 

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Not sure if this guy is actually 26 or not

I try not to generalize people at all because I truly believe in the whole "to each his own theory." Hello, I am a Sociologist who learned that the world is one big salad bowl and I truly believe this as well. When it comes to dating, I try to be the same way. You have to at least know a little bit about a person before you can say you aren't interested.

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iphone Sleaze Detector App good for singles?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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I don't "i" anything. Translation? I do not have an iPhone or iPod. It's not that I have anything personal against these super high tech devices or anything. Really, it's more that I am a faithful Verizon customer and I believe there are plenty of other neat-o gadgets that will play my music that cost a whole lot less.

 

 

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Chicago's Top 16 Most Eligible Bachelorettes

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Ever wondered where all the great single ladies in Chicago are? Well there is no need to look any further. Get ready to swoon and wipe up the drool fellas, because here are Chicago's top most eligible bachelorettes for 2009.

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Cocktails and Clay at Hyde Park Art Center

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

 

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Hey ladies! Need something to do this weekend? Check out Cocktails and Clay at the Hyde Park Art Center.

Every second Friday of the month the center puts together an evening of clay, drink specials and of course a little live DJ music. Clay sessions last for 45 minutes and the whole event lasts from 8pm to midnight. What could be sexier then other local singles, fun with clay molding and a few cocktails??

 

To find out more about the event click here.

To check out the Hyde Park Art Center and see other events that might interest you click here.

Just wanted to catch up and by the way I'm engaged

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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The other day I met up with a guy I know at Delilah's. We had a few beers and ended up swapping a few crazy dating stories. Lately, I have noticed that as I have started writing about single life more and more people have started sharing their stories with me (especially guys). This is definitely a great thing and I am by no means complaining. I enjoy listening to other people's stories and it is part of the reason I started writing in the first place. Plus, it makes for great conversation as well.

 

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First Fridays at the MCA

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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© Jeremy Atherton, 2006

This past Friday I had a chance to check out First Fridays at the MCA. First of all, I think the concept is a great idea. I mean mixing a little art, some drinks and food with a group of singles ready to mingle should definitely be the tools for a fun night right? Well, I have to say that I am not sure if I am overly impressed with the event itself.

 

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All The Single Ladies on ChicagoNow Radio this Saturday

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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What are you doing this Saturday? Well I can tell you what you should be doing. Listening to me on the radio. That's right folks. I will be on WGN 720 AM on Saturday at noon along with Sex and the Windy City.

 

What will we be talking about? Well everything about dating, relationships, sex and all the stuff in between that you are all curious about of course.

 

So tune in on Saturday. You can also listen to the show online here. Tweet us your questions @chicagonow or call into the show at 312-591-7200.

Show him a little skin, it's not a sin

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

According to a recent study women who show 40 percent of their skin are more likely to attract a man. This shouldn't seem all that shocking since men are visual people who appreciate seeing a little skin on a woman. Though, I will admit that I feel like 40 percent is kind of a lot. I mean that is close to half of my body.

 

The study counted each arm for 10 percent and then each leg was 15 percent, the torso was the remaining 50 percent (apparently your head doesn't really count at all here). If you wear a dress, essentially you have your 40 percent right there. So really, I guess that doesn't seem all that bad.

 

Be careful though ladies, because apparently if you show more then your 40 percent that will actually turn a man off. Apparently when you reveal too much it makes a man suspect that you are unfaithful. Yes, that's right, too much skin makes a man think you are one cheating floozy. Talk about stereotypes. Clearly I get that if you show too much skin that you can give off a slutty vibe. However, I don't think that's really an indication that you cheat.

 

I also have to say that we live in Chicago and I am not really sure how well this whole percentage theory stacks up against the winter here. Sorry guys, but hanging my 40 percent out when it's 30 below zero is not really my idea of fun. So I think I would have to save that for a night in. Hopefully you can cut me a little slack there.

 

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Adopt a guy on the internet

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Obviously, I am no stranger to internet dating but I found something today that might take it to the next level. Apparently now ladies you can adopt a guy on the internet. Yes, you read that right. Adopting a child? Yeah of course. Adopting a puppy? Definitely. Adopting a guy? Wait...what? I guess you really can do everything on the internet. Who knew?

 

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Thanksgiving survival for singles

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Yes, I know it may seem a little typical of me to write anything about how to survive the Thanksgiving holiday when you are single. What is there to survive exactly? Survival, to me, is more something you do when you are stuck in some awful situation and want to get out alive. You know like if aliens are invading or a meteor is headed straight for Earth.

 

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The rules of dating

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Anyone who knows me can attest for the fact that I have somewhat of a rebellious side which means that I don't really like to play by the rules. I am not really all that into labels or stereotypes because I honestly feel that people are people and we should just be ourselves. These are things that I really love about myself but that sometimes can make my dating life a little crazy.

 

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There is no (good) excuse for standing a person up

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Stood up. Two pretty ugly words right there. I am pretty sure that's one of the worst phrases in the dating dictionary. It's kind of like dropping the f-bomb in front of your Grandma on Christmas morning. The worst part of it is that you can't really see it coming. I mean I have had it happen when I literally just talked to the man a couple of hours before to confirm plans for the date. How does that even happen? Really.

 

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He's sorry for blowing me off (really)

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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As I have said before, I am a woman who  gives credit where credit is due. In light of some recent events, I sort of feel like I should tweak my thoughts on the guy from Facebook. Though, I can't really completely retract my opinion on the entire situation as a whole here. Frankly, what happened sucks and there is no denying that. However,  I do also know that doesn't necessarily mean the person sucks, people do make mistakes sometimes right?

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Smart phone feature smart for a blind date

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

Everyone has had a bad date; actually most of us have probably had more then one bad date. We are not just talking about the slightly unattractive date with the funky breath here. No, what I am talking about is the date where the thought of just sitting through a dinner with them makes you want to throw up a little. The total creep package - rude, obnoxious, not attractive, offensive personality, completely mannerless - you get the idea. These are the type of dates that caused the invention of the casual let's go have a drink predate so you can make sure you actually want to sit through dinner with the person.

If you have been on your share of dates like this, it's likely that you have a back up plan to get out of it. I am definitely a believer in the back up plan; it's a necessity ladies (and gentlemen). Of course I will openly admit that I have been a part of plans like this in all my years of dating.

Most people tend to go with a call from a friend. Slightly generic I will admit, but its fool proof. It may be a little harsh to plan your escape before you have actually met the date, but let's face it; there is no politically correct way to get out of this sort of thing. It's awkward and annoying no matter how you look at it.

I found this video on YouTube. The guy is a prime example of the date that deserves the back up plan. So take a look at it, have a laugh and hope you don't have to deal with this on your next date.

 

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Signal for sex on the first date

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Generally, I feel that you should go with the flow and do what feels right when on a date. Though, as a woman, sometimes I feel that there is a fine line between whats fun and what is just way too slutty. Which means there are things that maybe you shouldn't do on a first date. Back up for a second, there might be certain things you shouldn't do on a first date if you want a second date.

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Why is weight such an issue with online dating?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

I read an article the other day about the difficulties with meeting dates off the internet. As an avid online dater, I can assure you that it definitely has its issues. Then again, what method of dating doesn't? After all, if dating was fool proof, what would I have to write about?
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Avoid the excuses if you aren't into me

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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A couple of weeks ago I had a date. It was with a guy who sort of hit on me on Facebook. He read some of the things I had been writing on examiner.com and apparently thought I was attractive so he sent me a message. We chatted a bit, exchanged numbers, talked on the phone a lot and decided to meet.

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Why are you single?

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Jessica Downey

Coffee addict. The serial single girl. Jessica will give you the what’s what on single life and dating in Chicago.

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Oh the dreaded question that everyone has been asked at least once in their lifetime. If you are like me, you have been asked about your single status more times then you would actually care to count. It is likely to come up on a first date and sometimes it comes up before you even have the first date.

 

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