Does being a waiter get you any dates?
Um, nope. I've only been working a few months there, but I don't get any numbers or anything like that. Old ladies hit on me, which is kind of weird. Tell me I look like Todd English or Rick Fox. Most of the time it's not even my table. They just call me over from across the room.
Tell me about a weird or fun dating experience here in Boston.
I met this one girl through my friends and took her on a date and ended up having sex with her.
Yes? And... was this fun? Or weird?
It was fun and weird. Just took her out and ended up having sex with her in my car. It was cool. I just got of college so, that was great, except I had to fucking pay for everything. It's expensive. But it did pay off. I'm really lax in dating. I just haven't been a big dater. I dated this girl in college, but still had sex with other girls just because I could. She still doesn't know. She just texted me actually. I feel bad. But I'm never going to tell her, because one of the girls was her roommate. Her whole group of her friends would break up. It'd be really bad.
You had sex with her roommate? While they were roommates together? How did that happen?
They all went to a club, but this girl stayed behind — it was during spring break — and she just called me and asked me to come over. She started it, not me. It was fucked up, but the girl who I was dating was pissing me off. She was down at this club, not answering my texts...
So you fucked her roommate.
Yeah, it was really stupid.
And do you see yourself dating her monogamously now? Now that you're exchanging texts again?
Maybe. Just 'cause there's so many fewer girls around. In college, it's like a free for all. Girls are wasted every night, being idiots. And now, you really have to try. You have to take girls on dates and stuff. It sucks.
So you prefer the former lifestyle?
Eh, it started taking a toll on me. I just started feeling really stupid at the end of college. Braindead from all the drinking and smoking and partying. So I'm glad I took a break. But I don't really get girls. I just go with it. A lot of the time it happens to me, I don't have to do anything.
What's the craziest thing you've done to get laid?
I don't know. I did a lot of dumb shit. I used to drive drunk, pick girls up. I don't think I've done crazy things to get laid, but I've definitely had sex at weird times in inappropriate places.
You'll think I'm such an asshole. Well, it was at our first "day drink" at school — a Saturday where everyone wakes up and gets shitfaced — and this girl and I were just drinking and she goes, her words, "You want to go upstairs and have a quickie?" And I was sitting there taking a shot, thought she was joking, and then she was like, "Seriously," grabbed me and took me upstairs and I had sex with her at around eleven in the morning. And then right after that, I got a call from this other girl who I was hooking up with and she asked me to come over and have sex so I did. That was one in the afternoon. And then the girl I was kind of dating met up with me at around seven in the evening, and we had sex. And then this girl I used to hook up with called, and I went over around two a.m. and had sex with her.
There are only so many hours in a day! Four different women in one day!
Yeah, you've got to shower in between. It was pretty aggressive.
That's more than pretty aggressive!
I'd say three of them, I didn't even initiate it. Just kept it going, I guess. I was shitfaced all day.
Huh. Well, I was going to ask what the kinkiest thing you've ever done is, but…
I haven't really done any weird stuff. I've only had anal sex one time in my entire life. I don't even know who initiated it.