All The Single Ladies

Dating don't 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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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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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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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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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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Are women too picky?

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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 shopping for jeans

I've been thinking a lot lately about this whole idea that women are too picky. It's not a big secret that people often think women dump men for silly things like wearing white socks with black pants or brown shoes with a black shirt and so on. I've known many women like that and I can admit that there was once a time that I found myself saying things like that when I realized I was losing interest in a guy.

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I'm depressed I don't have your number

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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.

Invitation on a Slip of Paper

I have kind of neglected my OkCupid profile lately. It wasn't something that I did intentionally, it just really sort of happened. Though, I mean I feel like that seems pretty logical since I was busy planning my trip to New York and then I was actually In New York. Plus, we all know I have bad luck when I am busy and getting ready to go out of town.

Well, I came back and like any internet dating junkie I checked my messages. There wasn't really anything exciting there but while I was "online" I received two instant messages. One was from a fairly cute 22-year-old (the jury is still out on where I will go with that one) and the other was from a guy whom I have never met and haven't talked to in weeks for a few different reasons.

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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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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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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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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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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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A cattle call won't ever get you the girl

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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.

2 cows in a pasture

Last night, I read a fabulous post over on The Queer Guy Tells It Straight. The post was about men trying to pick up women from their cars and how this attempt doesn't ever (and really definitely shouldn't ever) work.

I have to say that he is completely right here, fellas. In fact, I would say that, as a woman, I don't find anything even remotely flattering about a man who does this. If you are a woman who thinks this kind of behavior is flattering you seriously need to check your standards on how you feel a guy should treat you.

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Sometimes it's not a deal breaker, it's just down right picky

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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.

View of a young man picking out shirts from his wardrobe
The other day I was sitting on the bus on my way home from work and there was a girl next to me reading a magazine. I have no idea what magazine it was but there was a section about deal breakers in dating for women.
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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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Please do not check out other women 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.

ThisIsTheLife.jpg

Anyone that knows me really well can tell you that there are certain things about my life that I am super anal about. For instance, I fold my towels all the same way and they are organized on the shelf by color. It's my system, always has been, and I don't like it when people mess with my system. When it comes to dating, however, I tend to be pretty laid back and open minded.

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Dating is a privilege not a right (part 2): You are not a princess

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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.

Princess.jpg

The other day, I read an awesome post from Single City Guy called Women Aren't Entitled to Anything which really made me think about how there are some women that feel they are entitled to certain behavior from men. You know, the whole idea that men should pay for everything, buy them gifts all the time, and generally worship the ground they walk on. I like to call this the princess behavior.
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Dating is a privilege not a right (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.

Who Am I.jpg

Let me start by saying that I am talking about both women and men here. You can call it my little disclaimer if you will, but I really feel this is a principle that applies to both sexes. Not that I am perfect (trust me I will be the first to name all my flaws if you ask me), but I personally feel pretty special when a guy I like wants to date me. So in return I like to try to show that as best I can.

When you first meet someone, they are generally pretty sweet and try to impress you, which generally continues at least through the first few dates. Sometimes, however, this nice thing stops and is replaced with the person's unwillingness to admit they like you. This generally happens because the person gets comfortable with the idea that you like them which then develops a cocky attitude. You know the whole idea that you like them so they can do no wrong.

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What's so bad about going to a strip club with a 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.

Sexy Stripper.jpg

If you've ever picked up a Glamour, you know they usually have a section about dos and don'ts. They provide a little entertainment/humor and are really just those little useless facts that might come in handy on your next trivia night. Well the other day I was browsing through the magazine and read that 69 percent of readers say going to a strip club with a guy is a don't.

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