All The Single Ladies

Romance Archives

How about we...Actually go on a fun 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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One of the most difficult parts of online dating can be planning the first meeting. Sometimes it seems like a guy might want more of a chat buddy than an actual date. And you end up chatting for weeks and weeks before meeting, if you even meet at all. Picking a spot to meet can be even more difficult.

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Valentine's Day Schmalentine'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.

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I have to be totally honest here - I am really not a fan of Valentine's Day. There's actually quite a few reasons really. And, no, none of them have anything to do with the fact that I am single because when I have been in relationships around the holiday I have felt the exact same way. 

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Stop making excuses

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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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About a month ago I wrote a guest post on That Happened To Me about a date that I went on. As you can read in the post, the date was pretty freaking awesome and it was the first time in quite sometime that I really wanted a second date. I mean truly wanted to see the guy again. But, the second date never happened even though he pretty much planned the entire thing with me.

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Dating advice I don't understand: Signs to tell he thinks you're the one

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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 read a lot of stuff on the internet. Some of it is really awesome and some of it I don't really understand. I mean, I comprehend what it is saying but it just baffles me. Yesterday a friend sent me an article called "5 Signs He Thinks You're The One" which I believe was published earlier this month in Cosmo. This would be a perfect example of an article that baffles me. And I know I am a little late to the game on this, but I really felt like I wanted to share my two cents.

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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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Guest Post: A little something about decorum

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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 I have an awesome guest post from my dear friend Dave Sorrell, also known as @rookiephenom on Twitter. I really love guest posts from guys because sometimes (or always) it's nice to get a little perspective from them. Now, we all know that I don't think there every guy feels the exact same way about things, but still it's nice to get their perspective.  Anyway, here he is talking about a little something called decorum.

 

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Guest post: Oh the weather outside is frightful...

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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 few weeks ago I wrote a guest post for a website called Cupid's Pulse. Well, I am super excited because one of their very awesome writers has so graciously volunteered to guest post for my blog as well. This post comes from Erika Mionis who is a staff writer at Cupid's Pulse. Erika is a student in Arizona who hopes to pursue a career in journalism. 

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Advice for a reader: Is he that 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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I recently received an email from a reader asking for advice. She doesn't want me to share her entire email with everyone so I am just going to give you the gist.

She recently met a guy from an online dating site and they have been spending time together. However she is a bit confused due to the fact that he's openly admitted that he is divorced, meets other chicks from the dating site, and is really hung up on woman he met a few months ago who currently has a boyfriend. So she wants to know if he is interested in her or just wants to be friends.

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Internet dating can be so complicated

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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 a message today on OkCupid. I am not positive if I would consider it an online dating message gone bad because it's definitely not the worst I have ever read. However, I am not really sure how I feel about it and it raised a few interesting thoughts/questions.

Here is the exact message I received:

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Could you date a guy who still lives with his parents?

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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 Dusting Houseplant

I love Sundays. Generally they are a pretty relaxing day for me. I drink a lot of coffee and write a lot. Sometimes I read and just try to relax. Actually, I am even known to cook a meal or two on Sundays. Another great thing is that Sundays are usually a great day for television, which is where I get to admit to watching some of the really lame shows that I actually watch.

I tend to be drawn to MTV occasionally on the weekends. There is often a marathon of shows like True Life or Made and what can I say, I am a fan of those shows for the most part. Hey it's a little better than my addiction to Teen Mom.

At any rate, earlier today I caught an episode of True Life which was about people who lived at home with their parents. I am pretty sure it's a fairly old episode of the show, but it's one that I hadn't watched before.

On the show there was a guy who was 30-something and still lived with his mom. He openly admitted to being a mama's boy and said he just hadn't had the desire to move out yet. He also openly admitted that he's never had a serious girlfriend and that he thinks it would be a little difficult to bring a lady friend home to his mom's house.

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In defense of the shy 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.

 

Man in boxers crouching

Recently I made a new friend. I kind of use the term friend loosely here as I have been engaging in a little flirtation with him. Read that as I have been flirting my ass off. He knows it and it seems to be pretty mutual.

Anyway, upon getting to know this guy, he has openly admitted to me on more than one occasion that he is a really shy guy - actually to be technical here he is a shy guy who is also on the clean cut side. This is generally the kind of guy that I have a really hard time meshing with and I know it's a problem for other women too.

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Chemistry is not the only thing that is important in a relationship

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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 mentioned a few times about how important chemistry is to me. Honestly, it's just something that I need in a relationship. And maybe it's a made up idea or something you use as an excuse when you just aren't that into a guy, but for me it is truly important.

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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 3: Things haven't gone the way I planned (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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So it's week three of the Date Night Challenge. And this week I actually had a date lined up. I say that like I am a little school girl or something but I was actually pretty excited. Frankly, there has been a shortage of really awesome guys asking me out on dates lately - I am not sure why that is.

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Win a pack of FlipMe dating cards

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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 anniversary for my blog was a couple of days ago which is a really exciting thing for me (don't worry I will post more about that later). So to thank all of my awesome readers I have another really fun giveaway.

FlipMe is a new and exciting way to date/meet people. In fact, when the people over at FlipMe contacted me to tell me about their service, I was extremely excited. As an avid internet dater, it's fun to mix things up a little sometime. After all, you can't put all your eggs in one basket, right?

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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.

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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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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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Date Night Challenge from 123Underwear.com: Week 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.

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No, that is not me posing

So the Date Night Challenge from 123Underwear.com is officially underway. Ever since my order arrived last week I have been extremely excited to actually wear what I chose. Yes, they sat in the box because I saved them for an actual date to wear them. After all, that is the point of the Date Night Challenge. Plus, I didn't want to let the newness wear off.

Technically the challenge was supposed to start with a coffee date this past Sunday but the date was rescheduled for last night. And it actually turned into drinks which seems more like a nighttime sort of thing anyway. Plus given all the other events of my weekend I didn't mind having an extra day.

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It's time to talk about (my) underwear

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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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If you've ever been underwear shopping with me you know that I am kind of picky when it comes to underwear. And when I say picky I don't mean that I have to buy the most expensive things or a specific name brand, I just mean that I tend to only like certain kinds. I definitely try to have some sexy things but I also like to be comfortable. 

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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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You have to pick up the phone 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.

Young Man with Cell Phone

A couple of days ago I read an awesome post over on the Queer Guy Tells It Straight. The post was about text dating, in other words people who use texting as their main form of communication while dating. I honestly couldn't agree more with his post and it made me want to throw my two cents in.

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First impressions are exhausting

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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.

My niece and nephew came for a little visit this past weekend. We planned to go to the Museum of Science and Industry and the Lincoln Park Zoo. As we were getting ready to go on Saturday, my niece picked out what she wanted to wear. She chose a pair of black leggings with a pink and black striped sweater dress mainly because I was wearing black leggings and a black dress and she loves to wear outfits that match what I am wearing. She also decided that she wanted to wear the socks that I bought her when I was in NYC.
 
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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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Too much too soon: What's the point?

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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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We've all met (and dated) the too much too soon guy. You know the guy that you go on a date with and he talks about all the things you guys can do together. He's incredibly complimentary but in a way like no other because he makes you truly think about the possibility of a relationship. And not just any relationship, but a relationship with him. You become hopeful, excited, curious.

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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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Just be honest 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.

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Apparently things aren't going to work out exactly the way that I thought with Mr. Google. I know that generally things don't work out the way you plan them and that's not always a bad thing. Life is full of surprises and some of them are fantastically pleasant. But no matter how aware you are that things can go bad, it's still disheartening when it actually happens. Actually, it pretty much sucks.

I am honestly not even sure where to start. It's just one of those things where I thought things were going one way but turns out they were going in the complete opposite direction.

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Guest Post: Apples to apples

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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 am officially back from New York which means it's time for a new post but first I want to share a guest post from a blogger that I was recently introduced to.

Disaster on Heels has been chronicling her single life in Chicago since she broke up with her boyfriend one year ago.  When she's not adding vitamins to Lean Cuisines to enhance nutritional value, she's having disastrous encounters on Match.com and OkCupid.  Today, in honor of the one year anniversary of her online dating profile, she has decided to celebrate with All the Single Ladies.

To keep up with the daily disaster, connect with Disaster on Heels on Twitter or on Facebook.   

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Long distance relationships: Yay or nay?

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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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Long distance relationships aren't for everyone. I've been in my fair share of them to know that sometimes they suck. You have to schedule time to be together and sometimes you miss out on stuff. And you have to rely so much on verbal communication because you can't be physically together when you want to be.

Sometimes one (or both) people involved don't even realize that they can't handle it until they're actually in a long distance relationship. When I was in college and moved to Indianapolis, I had a boyfriend. I think we lasted a month or two before things started to fizzle and ended with him telling me he just couldn't handle the distance because he didn't want to have to worry about when he would see me again. So even though I was fine with it and he assured me he was fine with it, he ended up bailing.

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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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You're happy, so why cheat?

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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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Cheating happens. Not that I am trying to say that I condone it or excuse it but the fact of the matter is that is happens. One thing that I really don't understand about cheating is why people do it. Actually, correction I do not understand why people do it and then go on and on about how much they love their significant other (and how happy the person makes them).

First things first, let's clear up the things that I understand.

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I'm independent but that doesn't mean I can't be (a little) dependent

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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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On more than one occasion I have had guys mention how there are certain characteristics they feel might keep me single. Then a few weeks ago at one of the ChicagoNow tweet ups, a friend asked me if I felt I had any habits or characteristics that I thought attributed to the fact that I am single.

There are things about me that I know certain guys don't like. I don't say that to make me sound bad or to imply I am a bad person. Honestly, I don't think that I am supposed to be liked by everyone and I certainly don't think that everyone has to want to date me. At the end of the day I just believe that people are who they are (though I am definitely not saying no one can change ever).

However, I know there is one thing that can be problematic at times. I want to avoid sounding completely cliché here, but the fact is that I am a very independent woman and tends to be a problem in the dating world. Though sometimes I feel it's because it often leads to so many incorrect assumptions.

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You like me but that doesn't mean you have to like everything about 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.

Mr. Google and I were talking the other day. Yes, that means he is still kind of in the picture. That is, as much in the picture as one can be when he is a few states away. Anyway, we were talking the other day when he said what I would like to call an over compliment. And it really made me think.

Here is the abridged version of the story. There are some not so flattering pictures of me on Facebook. I consider them not flattering because my hair is a much different color than it is now. Clearly I am totally going to out myself here, but no, the brunette is not natural. Honestly, I detest my natural hair color (on me). Mr. Google confessed that he discovered the pictures of me on Facebook and said that he thinks I look beautiful either way.

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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 you are just not the right (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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There is something I have kind of noticed a lot lately in some of the guys I have been meeting. A lot of them seem to have this whole "I am the man" kind of attitude about them just because they think they are a nice guy. I guess just being nice should be enough and apparently I am a total ass for even questioning if I want to date them.

Now, wait a second here, because I know what you are probably thinking. I am not advocating anything against dating nice guys here. So let me make it clear here that I am not saying that a woman should choose a bad boy over a nice guy. Rather, I am saying that a woman shouldn't want to date a man based solely on the fact he is nice. There is more to dating and a relationship than that.

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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.

 

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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.

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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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An update on my quest for a summer fling

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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 woman

A little over a week ago I wrote a post about how I was contemplating a summer fling. It was pretty much a unanimous vote amongst my readers and followers on Twitter so I decided that I should do it. Since everyone has been asking for updates I thought I would give everyone a few little details on what's been happening.

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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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New weekly feature: The single lady blogger is shaking things 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.

Young Couple Speed Dating

You might have noticed that I didn't post any date ideas yesterday. And no, I did not forget about them nor am I a slacker. I have just decided to shake things up a little with a whole new weekly feature.

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Planning a date in Chicago? Here are this week's spots

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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.

This Photo Shows The Hot House And Employees Tending Plants In Chicago At The Lincoln Park Botanical Gardens. Lincoln Park Botanical Garden Employees Tending Plants

First of all, let me apolgize for not posting any spots last week. However, I do have some really fun ideas this week including some festivals and great dining deals. So if you are planning a date, here are some great spots to check out.

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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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Planning a date in Chicago? Here are this week's spots

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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 Heart U

Chicago Center for the Performing Arts
777 N. Green St.

Fridays at 8 p.m. (ends June 25)

Kind of a romantic comedy, only better. A sketch revue about romantic relationships. Cost is $10

Chef's Cooking Class

Wave
644 N. Lake Shore Drive

June 5 from 2:30 p.m. to 4:30 p.m.

Executive chef Kristine Subido leads a culinary demonstration on how to make Indian and Middle Eastern street food followed by lunch. Includes wine pairings, one cocktail and recipes. Cost is $60 and RSVP is recommended.

Eastside Millennium Art Festival

Michigan Avenue and Lake Street
100 E. Lake St.

June 4 from 12 p.m. to 5 p.m.
June 5 from 10 a.m. to 5 p.m.
June 6 from 10 a.m. to 5 p.m.

It's summer, so why not try one of Chicago's many festivals? Here you can browse works artists including ceramics, fiber, glass, jewelry, sculpture, mixed media, painting, drawing, photography, wood and furniture. And the best part? It's free.

Italian cooking class

312 Chicago
136 N. La Salle St.

June 5 from 12 p.m. to 2 p.m.

Yes, I know another cooking class. Learn how to make homemade pastas with executive chef Luca Corazzina and his mother. Includes appetizers, recipe cards and a bottle of olive oil to take home. Cost is $45 and RSVP is required


 

Planning a date in Chicago? Here are this week's spots

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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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So my man Andy Avalos on NBC told me that it will be close to the 80's this weekend. For the city folk that probably means somewhere around 72-ish. Point being that we have a nice weekend coming up in Chicago. So if you are planning a date this weekend then check out some of these ideas.

Also, I say it's a great weekend to take a walk on the lakefront or check out the Lincoln Park Zoo or ven better, head out on Sunday for brunch. Don't know where? Well have no fear because the Queer Guy Tells It Straight has you covered with his weekly brunch spot.

Happy dating!

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Planning a date in Chicago? Here are this week's spots

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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 Having Drink on Date

There are so many things going on in Chicago this weekend it was hard to choose. Most of this week's spots seem to be centered around budget dating. Let's face it, who doesn't love having a great time and being cheap (in a good way) in the process. So there is no excuse. Grab a date and get on out there and have a great time.

 

Happy dating!

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Woman calls off wedding and refuses to return the ring

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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 Woman Displaying Diamond Ring
The other day I stumbled on an interesting article on Powder Room Talk which talked about what you should do with the ring when calling off an engagement. The article stemmed from a news story about t a woman, named Colette Dipierro from Staten Island, who refused to return a $17,500 ring to her ex-fiance after calling off the wedding.
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Survey Says: One in ten people wouldn't mind a text during sex

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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 Taking Bath Together
Technology is a pretty big thing lately. As an avid Blackberry user and fan, I will admit that I love that I have access to everything anytime I want. I also have to add that I am pretty good with keeping it balanced - I put it away on dates and limit its use when I am with family. Which is why I was really surprised when a friend sent me an article about how one in ten people (under the ripe old age old 25) would not mind being interrupted by a text message during sex.
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Planning a date in Chicago? Check out this week's spots

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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 People by Bar at a Party

Here you have it, this weeks awesome date spots.

And don't forget to come out on April 10th to the singles night that Sex and the Windy City and I are hosting.

Happy Dating!

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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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Planning a date this weekend? Try one of this week's spots around town

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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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There are some fantastic things going on this weekend. So grab a date, brave the cold and get out and have a great time.

Happy dating!

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Are Chicagoans really anti-romance?

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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.

Anti Love.jpg

I recently read an article in Chicago Magazine that talked about how Chicagoans aren't really romantic. According to the article, Chicagoans do not think that poetry, flowers, restaurants, snowstorms or views to be particularly romantic. It seems that things like sunsets, ice skating, or candles don't woo us all that much either.
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