Missy, 30

What do you do for a living?
I run service groups for college students in impoverished areas.

Does that ever get you dates?
Of course. You tell people you're a do-gooder and they're like, "Oh my God, I want to sleep with you."

That's happened?
Yes. Right after Katrina, I was at a bar talking to this guy, and I was like, "Yeah, I'm taking this group of twenty passionate students from Americorps down to New Orleans to help rebuild." He looks at me and goes, "I should sleep with you to thank you." And I said, "No, you shouldn't sleep with me. You should actually go down on me for five days in a row." He looks at me and he's like, "You're on." And that happened!

You got oral sex for five days straight?
Yeah, at 8:30 every night like the news. I was like, "When Al Roker gets on, so do you." And I didn't think this guy would go through with it — it was just a line. But, at the end of the day I was like, "Score!" I had a roommate and I told her that every night at 8:30 she needed to go away.

Have you ever been offended in the bedroom?
Yeah, one time in New Orleans, I was with a guy who said, "I'm your hurricane and you have to tame me." I was like, "Are you kidding me? There's like millions of dead people because of you!" I got really angry. It was very offensive. And one guy was like, "Since you're such a do-gooder, do you mind if I fuck you in the ass and do me some good?" Like, really?

Have you ever offended anyone in the bedroom?
I'm perfect! How could I offend anyone in the bedroom? I'm a do-gooder! No, I've never offended anyone, though I have been a little more aggressive than other people. Because what I've learned since being a very little girl growing up in Brooklyn, is that if you don't ask for what you want, no one will give it to you. But if you tell them what you want in a mommy kind of way, they get offended and stop doing what they're doing. I did once offend a man by asking if I could bring a friend with me.

Male friend or female friend?
He assumed I meant a male friend, but I meant a female friend. But he was like, "What, I'm not good enough?" He went immediately to the male thing. I was like, "Okay, you like boys, I get it, but that's not what I was asking you."

 

 
Barry, 26

What do you do?
I live in New York and sell diamonds.

Does that get you dates?
Yes, I'm the Israeli Barry Manilow that sells diamonds!

How so?
Well, my boss tried to set me up with one of the buyers. He wanted me to hook up with her to try to get her to sell us a bunch of diamonds.

So you got pimped out?
Yes, he tried to. I didn't agree to the terms.

Was she attractive?
She wasn't!

What if she had been?
I might have done it, but not for the business aspect.

What's the best date you've ever had?
I met my girlfriend through work at a Halloween party. We both hooked up with different people early in the night, but ended up with each other at the end. We both went there only because we each knew the other would be there.

Any psychotic exes?
I dated a girl for a year and a half, but after I broke up with her, she started calling me drunk from different places with her new boyfriend. And there was another girl I went on four dates with who — well, the first time I went to her house, she asked me if I needed a condom and pulled out a shopping bag full of them. There were at least 500 condoms in there. Every variety you could think of. I was very afraid for my STD situation. The second time I met her, she wanted me to come to Maryland with her to meet her family.

What's the craziest place you've had sex?
An Israeli military base near of all my soldiers. I served for three years. Towards the end of my service — I was a commander, so they sent me to a recruiting base to help direct the new recruits. There was another girl from the military police I was working with. It was late at night. We ended up inside the office of our high commander and started having sex. And all the soldiers outside couldn't fall asleep because of the noise. When we came out, they were clapping.

 

 
Carolyn, 27

What do you do?
I'm a fashion designer.

Does that get you dates?
I've been with someone since I was seventeen — we've been together for ten years! We were high-school sweethearts.

Was there ever an in between period?
No, but we went to different colleges and I was constantly commuting back down south for four years just to see him.

How is it going out to bars, do guys ever hit on you pretty badly?
One guy literally came up from behind me, and whispered in my ear, "Asian persuasion!" I swear, the hairs on my back stood up — it was so creepy! Anyone who says that is a douche.

If you were single, who would be your type?
Typically, I like the bad boys — so I'd go for that if I were single.

What is it about bad boys?
You always want what you can't have! And they make it so freakin' hard! Plus, I think girls like being tortured a little bit. They like the chase, because once they get the guy, they're like — next!

Interviews by Sean McGurn and Laurel Stye. Photography by Sean McGurn.