Mary, 29
 

What do you do for a living?
I'm an executive assistant in the accounting industry.
 
Does this job get you laid?
Not really. I work with sixty people and eighty percent of them are over the age of forty-five.
 
Too old for you?
Yeah. The oldest guy I've ever dated was thirty-five, and that was still a little up there for me. There are too many differences between people when there's that much of an age gap. I also don't get laid at my job because everyone I work with is married and have kids. Talk about a turn-off.
 
Which of the seven deadly sins best describes you?
Pride. I like to be right all the time. I don't like to admit my faults.
 
What faults do you have?
I get bored very easily. I don't talk about my feelings enough in relationships. I play the role of the guy too much, I guess.
 
What is your deepest, darkest fantasy?
I've always wanted to have sex in pouring rain. And we'd be outside on a picnic table or on the hood of a car or something. It looks hot in the movies.
 
Do you have any sexual regrets?
Probably the first time I actually had sex. It was really awkward and uncomfortable. He didn't know where he was going, if you know what I mean.
 
I don't.
Yes, you do. He aimed a little low on the first...  plunge.
 
Oh. Ouch.
You're telling me. Even though I don't regret losing my virginity, I guess I regret not looking for a more... what's the word?
 
Experienced?
I regret not having a more competent partner for my first time.
 
Can you count on both hands the number of sexual partners you've had?
Do toes count?
 
No.
Okay, I need my toes too.
 
Does money matter when it comes to love?
Not at all. I mean, it helps, but if you really love someone, then you love that person no matter what. For better or for worse. Chris Rock had a really good line during one of his shows: "You gotta love the crust, the crumbs, the tiny crumbs at the bottom of the toaster. That's what real love is."

 

 
Sebastian, 24

What do you do for a living?
Audio postproduction for the advertising and entertainment industry

Does the job get you laid?
It can, but there are a lot of sucky people in the industry — people who know that they're higher up and treat everyone below them crappy. And then there are... I don't really know how to explain it. Not cool coworkers. The show Entourage comes to mind.

What is your deepest, darkest fantasy?
To sleep with a mom. But not like a young woman who just had kids. A more legit mom.

What does a "legit mom" entail?
Like an older mom. I won't put a number on it. But definitely older. Forty-plus.

Do you have any sexual regrets?
No, because I wouldn't ever do something in bed that I would potentially regret. Or if I did, I'd just roll with the punches and learn from the experience.

Do you have any dating dealbreakers?
Hard drug issues. More than the occasional cigarette. Oh, and STDs.

What is your favorite sexual memory?
I slept with a professor back in college.

Was she a mom?
Not to my knowledge, sadly. She was only in her upper twenties.

So it wouldn't have been "legit."
Right. But she was engaged, and no longer is... but that's not because of me, I don't think.

What happened?
Technically she was a teaching assistant. But she had her own office and was the only teacher for the class. I was always really quiet in class, because that's just how I am. And it just so happened that we had a mutual friend. So one night I went to this house party and she happened to be there. Because I was drinking and kind of came out of my shell a little, we really got to know each other. Long story short: everyone at the party ended up passing out except us two and we started making out on the couch, which eventually led to my apartment, which was conveniently next door.

Can you count of both hands the number of sexual partners you've had?
Fucking sex or hooking-up sex?

What's the difference?
Well, hooking-up sex is like getting a blow job, where as fucking sex is...

I get it. Fucking sex.
I don't know the exact number. But it's around there. Give or take.

 

 

Kelly, 27

What do you do for a living?
Bartend.

Does this job get you laid?
I don't know yet. It's my first day. But I'm hoping so. I met a few people at the bar that I'm at now, so, yeah, I hope so.

What's your deepest, darkest fantasy?
I like to dress up. I have a lot of slutty costumes. I don't think I'm very good at acting — it's more just wearing something specifically hot to turn my partner on based on his desires.

Do you have any sexual regrets?
There was this guy who I worked with at a different bar. I didn't really want to have sex with him because I wasn't really attracted to him. But I did anyways.

Why did you?
He was older, and he just took control of the situation I guess. He didn't cross any boundaries or anything like that. But I just wish I hadn't felt so pressured to do something I didn't want to do.

Do you have any dating dealbreakers?
I love guys who are into sports. I don't like pretty Jersey Shore type guys who pop their collars and shit. I love cargo pants, t-shirts, and hats. They have to have nice teeth and good breath. If you don't have that, how am I ever going to want to kiss you?

Does money matter when it comes to love?
Not for me. My last relationship, we started off making lots of money. And then when the economy went to shit, we lost it all. We still loved each other though.

Do you have a favorite sexual memory?
I like to do it random places. If it comes up then we just do it. We were on vacation and we did it in a cabana, and there were people walking around who we had to try to hide from. Or there was this other time we were driving home and the closest thing we had was a side street, so we just turned down it — it wasn't exactly a private drive — and turned the car off. And there was one time behind a supermarket. But I guess my favorite is when we did it while driving.

Like the movie The Chase, with Charlie Sheen and Christy Swanson?
Yeah. We were on the Garden State Parkway. He was driving and pushed his seat all the way back. And I just climbed on top of him.

I hope he was driving slow.
I don't really remember. All I know is that I wasn't going slow.

Interviews by Sarah Schwab. Want to talk to strangers in your neighborhood? Email .