All The Single Ladies

Dreadful dating Archives

If you don't want a second date then don't talk about it it

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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 last couple of dates that I have been on have been pretty good dates. Actually one date was pretty awesome and fabulous and you can read about my thoughts on all of that over here. At any rate, the dates were pretty good and I sensed that the feelings were somewhat mutual since each guy mentioned what we should do on our second date.

Well, here it is weeks later and I have yet to actually have those second dates.

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Online dating messages gone bad: Ima stick it in ur...

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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 received what I believe is probably the tackiest message that I have ever received on a dating site. I was actually debating on if I should write about it because honestly I am not sure if I can talk about the message without being crude. And while I like being a sarcastic and maybe even a little witty on this blog, I tend to steer away from crude. That is saved for drunken Wednesday night dinners with my friends, you know where it's not written for the entire world to see (sorry mom).

At any rate, I talked with some friends just after I received the message and they all thought it was a little hilarious and quite tacky as well but I still wasn't sure. Well then, when I logged into OkCupid the other day only to see that I had received the exact same message it became clear to me that obviously I needed to write about it. I mean clearly the OkCupid Gods were telling me that I needed to, right?

Here is the exact message:

Subject line: Blank (apparently you don't really need a subject for this sort of thing).

Message: ima stick it in ur ass

I guess he kept it simple and went straight to the point, right?

Now, the first time he sent me this message I thought - how does a person respond to that sort of thing? I mean should I thank him for being so willing to stick "it" in that area of my body? Really, thanks buddy because not every guy is that into that sort of thing so I am glad that you are putting it out there just to make things clear.

I guess since he is sending me the message again he wants to make sure to get his point across. I get it, really, it's loud and clear. Though I am mildly concerned here, I mean there are no pictures of my actual ass on my OkCupid profile, so how does he really know he wants to stick it there? Not that I mean to sound like I am insulting myself or anything (I happen to think my ass isn't half bad) but how do you really know what you are getting into here?

Then, of course, the thought also occurred to me that maybe he just sends this message out to mass quantities of girls on a daily basis. But frankly that thought kind of scared me a little so I had to stop thinking about it.

Then an even worse thought came to me. What exactly is he planning on sticking there? I mean it's implied and we can all guess what "it" is. But to be technical he doesn't specifically say so I might need a little clarification here just to be sure.

I get that some guys (and girls) are just looking for that sort of thing. And let me just say, for the record, that I find nothing wrong with that at all. To each his own. By all means, really. I also appreciate brutal honesty so I guess I should thank him for that. Clearly I would not want to be out to dinner with him and have him drop a line like that just before they bring us the appetizers. I mean, talk about awkward, really. Though really, couldn't you have just simply asked me if I am cool with casual sex like everyone else?

Plus, I kind of feel like that sort of thing should be more of a question. Shouldn't it? I mean unless of course we are fooling around and you know for a fact that I am into that sort of thing. But that's not something you can really get from a person's profile on a dating site. Then again there was also a time that I didn't know a guy could pick up that I looked like a girl who was DTF (link to post) from a dating site either. So clearly I am the crazy one that is missing something here.

Trust me, I am super open minded about poor messages on dating sites. But really, I think this goes a little beyond a message that just doesn't thrill me all that much. I honestly can't see how any person can sit down to write a message and think "this will get me a date (or laid)". Clearly it got my attention but not in any good way. So even if you were looking for just a little romp, you failed buddy really.

Moral of the story? If you send me a message like this, I can think of plenty of places for you to "stick it" that aren't anywhere near me or my ass.

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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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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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Online dating messages gone bad: If I can't understand you I will not respond

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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.

Close-up of a young man working on a laptop Horizontal

The other day, I realized it's been a little while since I have shared one of the awesome really bad messages that I receive from guys on online dating sites. Honestly, it's just been quite sometime since I have been blessed with some entertainment in my inbox. Well, clearly the internet dating gods (or whoever it is that decides these kind of things) realized this and decided to throw me a bone.

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I'm a real man and I don't play games

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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.

Side profile of a young couple playing scrabble

It seems like every time I am online looking through profiles on a dating site that I come across at least one guy that talks about how he doesn't play games or how he is looking for a girl that doesn't play games. This is something that I don't really understand.

First things first, some of these guys have a pretty awesome profile. I mean they talk about things they like to do and I feel like maybe this guy could be kind of interesting. But then, there it is "I am not looking for a woman who plays games" or "I am a real man. I don't play any games."

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Sometimes a guy comes back for more

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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.

 

Screaming woman

Remember the guy from this post? Well he is back again. And as much as I would love to say that he turned out the be some really awesome guy, I am pretty sure I have to report that he is still the same. He sent me an IM the other day. At first I wasn't going to respond but he threw out an I'm sorry and I figured what the hell.

Now, let me just say here, that, yes, it does take more than an I'm sorry. But at the same time, I firmly believe that sometimes people are truly sorry and I genuinely want to believe in the good in (most) people. Plus, I mean technically I don't totally know this guy so I feel like it's important to give him the benefit of the doubt.

Well, I have learned my lesson with this guy. I mean really, I have truly learned my lesson.

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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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A spade is a spade

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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.

Senior man holding the ace of spades

A couple of nights ago, I had the opportunity to meet with the very talented blogger/writer Disaster on Heels. We had a pretty simple plan - flirt with some guys, celebrate National Singles Week, and of course enjoy the $2 beer special at the Kerryman. The night ended a little early when she realized she had lost her wallet which made her believe that she was living up to her name as a disaster (you can read more about that over on her blog).

She was more worried that she was coming across as that really bad date. You know the one where the person "forgets" their wallet so the other person has to pay. However, the bill was only a mere $20 so clearly that was not her plan. I was really just worried about her finding her wallet because I genuinely felt terrible for her. Plus, when the subject of my upcoming birthday came up she assumed I was turning 25, so I am pretty sure I would have forgiven her for anything after that.

At any rate, our quick lap around the bar to meet and mingle with some savvy single guys was pretty unsuccessful. We tried and I mean really tried but the only somewhat attractive guys were a group of three early 20 something's, one of whom was wearing a pink polo shirt. I wasn't even actually sure guys did that anymore and DOH mentioned you shouldn't do that after Labor Day. And she was a little distracted by the wallet situation. Can you blame her? That is one of my fears right there.

However, earlier in the evening, as we were about two beers in, we were chatting about the chaos (aka our internet dating lives) which obviously led to story swapping. I talked about a guy that I recently met and as I was telling the details I really started to think.

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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.

side profile of man sitting on a couch with his arm around a woman's shoulder

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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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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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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If a woman says she's not interested that means she's not interested

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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 Laughing

A little over a month ago, I talked about the guy who threatened that he was going out with other women because I was too busy to meet him. Well, he is back. Actually, to be quite technical he's made a few guest appearances here and there over the past month

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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.

Fishnet stockings

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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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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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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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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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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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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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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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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Just because he's ending it doesn't mean there is anything wrong with 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.

Man and Woman Talking in Cafe

Break-ups are tough. No one really likes to hear that someone they like doesn't want to date them especially when you think things have been going just fine. So why is it that when we are getting dumped that we tend to make things even harder on ourselves by picking at all of our little flaws?

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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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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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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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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.

Dusty Phone.jpg

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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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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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.

Guy on phone.jpg

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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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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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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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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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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