So I did some online dating a few years ago. Right before I swore off it (and actually, the reason I was swearing off of it), I went out with a guy let’s call….. Derek. That’s not his real name.
So I had this free profile posted in our local, hipster-friendly newspaper. Derek (a pretty hot masseuse) sent me a message. Now, I’m not really big on emailing for weeks and then meeting each other. It’s way easier to lie about yourself in an email than in person. So I arranged to meet him for an afternoon coffee at a local (but not so local as to be too near my apartment) coffee shop. I set up my safe call with a friend, let a couple people know where I was going to be (if you’re reading this, Mom, you can see I was totally responsible and smart!).
I got there early, so I could pick a table that was within sight of the counter and other patrons, got my own coffee, and settled in with my book about Chaos Theory (that’s how I told him, and the couple others I saw, to find me. Again, it’s shocking I’m still single, right?).
Derek showed up pretty much right on time and we started in with the typical blind/online date questions.
I’m getting ahead of myself. Let me give you the info in Derek’s profile:
Age: 38 (I was 26. It was kind of a big age difference at the time, but I didn’t see this being a long-term thing… I just figured a couple dates couldn’t be too bad)
Neighborhood: Bucktown
Profession: Masseuse (I’ll admit that this factored into me agreeing to meet him)
Status: Single
The easiest way to do this is to just put the pertinent parts of the conversation in here. Let me emphasise that I am not exaggerating here. These are actual things he said. Italics are what I was thinking at the time, not current interjections.
Derek: I should probably tell you that I fudged on my age
Mairin: Really? [shit] How old are you?
Derek: I’m 39. But I just turned 39 and I just don’t feel that old. So I changed my birthday in the profile so it would still say 38.
Mairin: Huh. [what a stupid thing to lie about. not a good sign. i wonder what else he’s lied about?]
Derek: Oh, and I should probably mention that I’m divorced.
Mairin: Wait, but your profile said you were single. [being divorced isn’t an issue. it happens. not too keen on all the lying though]
Derek: Yeah, well, technically I’m single though, right? It was a long time ago.
Mairin: There’s a reason that “single” is an option and “divorced” is an option.
Derek: Does that bother you?
Mairin: Lying bothers me.
Derek: Well, then I should probably tell you that I don’t really live in Bucktown.
Mairin: Wait, but that’s what you listed as your neighborhood!
Derek: Well, yeah, I don’t actually live in Chicago. I live in [name of town about 2 hours from Chicago, let’s call it Loserville in Derek’s honor]. But when I did live in Chicago, 10+ years ago, I lived in Bucktown. And that’s where I’d like to live if I moved back. But yeah, I live in Loserville with my mom and older brother.
Mairin: (rapidly drinking coffee so as to end date) So they live in that town too?
Derek: We all live in the same house. I had to borrow my brother’s car to get here today.
[WARNING! WARNING! WARNING! WARNING!]
Mairin: [let’s change the subject to something less loser-y. this guy has to have at least one redeeming quality] So how long have you been a masseuse?
Derek: Oh, only about 6 months
Mairin: Really? What did you do before that?
Derek: Well, before that is when I was living in Detroit. Mostly I grew and sold massive quantities of high-quality marijuana.
Mairin: … [shiiiiiiiiiiiiiiit]
Derek: It’s the perfect place to do something like that, because police there really have bigger issues to worry about than busting people like me.
Mairin: … [is he really trying to use, “i was never busted for my illegal activity” as a positive quality?!?]
Derek: And it’s not like I was selling to kids or anything. I only sold to dealers.
Mairin: [oh, well in that case.... ] Well, I had really better be going. I’ve got this protest that I’m going to with my friend. The one who called. The one who knows where I am and who I’m with.
Derek: Oh, some friends of mine wanted me to meet them at the protest, what a coincidence.
Mairin: Haha, how strange. Well, have a good time, I’ve really got to get going.
Never saw him again. He actually emailed about 8 months later. I was happy to tell him I was otherwise occupied. Besides, it’s hard to go out with someone when you don’t know when he’s going to be able to borrow his big brother’s car.
Got a bad first date story? Please, help me feel better about myself and share it in the comments 
I met a guy online and his profile was hysterical. It was witty, somewhat sarcastic, and every so slightly cynical (just the way I generally like it.) So, we decided to meet at a bar in Wicker Park. He told me it was a place he frequented, but I didn’t really pay that any mind. I have my own establishments that I frequent and everyone knows my name and it’s no big deal. I do not in fact have a drinking problem…I don’t think. Anyway, I digress.
I arrive and he’s already there. I sit down next to him at the bar and he calls over his bartender friend and orders me a drink. I start the small chit chat, and he at some point in time in the first five minutes works into the conversation that as long as he’s not at work or on his way to work he sees no reason to be sober. In fact he had had 3 drinks before I even got there. OK!?
He then finds out I work for a church and turns the conversation into this completely cynical attack on organized religion. The conversation works its way into cynical attack after cynical attack on everything I hold dear. But, I’m a schmoozer and can hold a conversation with anyone without being easily offended. We both knew full well that this was not going to go anywhere, but against our better judgment decided to have dinner after drinks. That was the original plan, so we were just sticking with it. We were going to Peace, and I wasn’t about to pass up some cynical asshole paying for delicious pizza even if it did mean a few more minutes of awful conversations.
Long story short, he ran out of things to bitch about somewhere in the middle of dinner. Shortly after the bill arrive and he gave his card to the waitress, I excused myself to use the restroom. When I came out of the restroom the waitress came running up to me: “Oh there you are. I have your purse behind the bar.” (yes, I left my purse there. There wasn’t anything much of value, my phone and wallet were in my pockets. And he was an ass, not a thief.) I looked at her confused and then looked at where we were sitting to see two new people sitting there. I looked back at her and said, “do you have my date, too?” She didn’t really know what to say. I gave him the benefit of the doubt and thought maybe he was just giving up the table so as to allow someone else to sit. But no, he had left altogether. No “goodbye”, no “it’s been real”, no “let’s never do this again, please and thank you.” He just walked out while I was in the bathroom. When I got back home I revisited his profile and at some point between when I first met him and when we went out he had changed the entire thing to reveal his true cynical asshole self. I only wish he had had the courtesy to inform me that his original lighthearted profile was a ruse.
The End!
OMG that’s awful!
I must say though, I love this thought: “We were going to Peace, and I wasn’t about to pass up some cynical asshole paying for delicious pizza even if it did mean a few more minutes of awful conversations.”
For anyone not in Chicago… their pizza really is that good
I totally remember you going on this date! Oh, such a good story!