Winston, 28

What do you do?
I just started working at a bar as of today. I'm also an aspiring novelist and columnist.

Does your job ever you a lot of dates?
I've been married for five years, and my marriage is now dissolving, so I haven't had a chance yet to pick up dates through my job.

How about prior to your marriage?
No, I've never ever gotten laid because of where I worked. Before I met my ex-wife, I worked at a coffee shop and a book store, a movie theater, and lots of places that aren't exactly sexy.

How would you compare your attraction to woman as a married man, compared to when you were single?
When I was actually married, my relationship with other single women was stressful, because I'm a naturally flirtatious person, and that doesn't tend to create a great environment inside the confines of a marriage. I was a good husband, don't get me wrong, but I am flirtatious. I talk to people, I laugh, I like to hug, all that.

Tell us one of your most interesting hook-up stories.
When I was nineteen, I met a girl via the internet, and she was very obviously interested in just hooking up, so I drove out to meet her. And when I got to meet her, it turned out her right arm was missing from the elbow down. But she was a beautiful girl, and I treated it as like a regular one-night stand. Nothing was changed to me, but I could tell that she was very self-conscious about the whole thing.

So the arm wasn't a dealbreaker?
No, and had it turned into something real, it wouldn't have been a dealbreaker anyway. But it was surprising at the time. I didn't expect it.

Do you believe in love at first sight?
I don't think I believe in love anymore. I had my heart broken in the relationship — the marriage — I was just in. It makes it hard to trust anyone now. Don't get me wrong, if you're in a committed relationship, and you're in love, good for you. I'm not trying to disparage what you've got going on, but for me, on a personal level, I'm a way more cautious now than I was a couple of months ago.

Where's the most daring or unusual place you've had sex?
I had sex on a ferris wheel only a few months ago. Like five or six months ago.

Explain how that works. Is that like straddling or doggy style or....
Doggy style, I guess. Her sitting on my lap facing the other direction. It's not quite doggy style. I don't know what you call that... sitting? But you don't have a lot of time, so it's kind of like sex expedited.

Was there a happy ending?
Yes. Actually, I think on both parts. I'm pretty sure. Guys never get to know for sure.

If you got a book deal to write about your sex life, what would the title be and why?
What the Fuck Am I Doing Wrong? And I think that's pretty self-explanatory.

 

Jayne, 29

What do you do?
I'm a nanny and aspiring writer.

Nanny, eh? Does that ever get you dates?
I think guys with kids, and guys who want to be emotionally coddled, tend to ask me out more than anyone else. It's the idea that I'm a caretaker or that I'll be sweet — and, I mean, I am sweet — but they have this idea that I'm going to take care of them and either be really good with their children or be their second mother.

What do you look for in a guy?
I want someone who's going to make me laugh, and can keep up. I don't want him to have to Google things I say during the conversation. If you're Googling words that I'm saying, I don't know that I want to date you.

What do you find physically attractive in a man?
I have a type, but I deviate from it a lot. I'm an equal opportunity employer. I have something that I really like, but that easily goes out the window if you can make me laugh or I think you're really smart. But physically, I like them to be way taller than me. Fit. There are so many things that are cute about guys: they have beards, or they smell good, or they have deep voices — I love deep voices.

Is the deep voice for the phone sex?
[Laughs] I think it's just because it's a very manly, masculine trait, and I think overall I would err on the side of masculine traits.

Is it possible to be too masculine?
A guy can be too masculine when his life is a competition with other men. If it's just about more muscles or a faster car. You never want to be involved with those guys, because you're always going to be an accessory. You'll never mean anything.

How do you impress a man?
I don't, really. I don't try to be anyone I'm not. I guess I like cooking for a guy, but I also like cooking for my girlfriends, so that's nothing special. I guess everyone peacocks a little bit. I probably flip my hair more around a cute boy.

How early or late in a relationship do you think it's okay to sleep with a partner?
I usually try to wait a couple of months. It sifts out the guys who don't really care about you, but also you build a rapport with someone, and it's not sex-related. Also, I am very skeptical about the health of anyone who would sleep with me without actually knowing me, and how that would affect my health if I slept with them. I haven't had a lot of sexual partners, so I tend to get emotionally attached to people. That's something I have to watch. I tend to date three to six months before have sexual interactions with someone, but I still talk to them about what it will be like when we do.

How does that work out in terms of...
I don't get laid a lot. [laughs] No one likes it.

 

John, 28

What's your job?
Student. I study literature.

Has your being a student ever gotten you laid?
Oh yeah, absolutely. All the time. I mean, in that I only date graduate students, because you're always around them: in the computer lab, in the library, studying.

How do you approach that situation?
Usually with some sort of pun — the dumber the better. That usually attracts people. Also, I think not talking about my work all the time helps a lot. If you're the least committed of the students, you seem the most real. You have to act like you're not really into what you're into.

What's an example of you being real?
Making a reference to a movie that's not high-brow, and acting as if I've seen it.

So you don't actually watch it?
No, of course not. Why would I do that? That's how real I am. [Laughs] No, but really, if I pretend that I saw something like Love and Other Drugs, or something with Natalie Portman in it, then that makes me seem normal. Even if I'm not interested in her movies, but people think I am, then suddenly I've transformed from a bookish graduate student into a kind of Don Juan.

Once you've established your realness, how do you make the next move?
That's where it gets really difficult. It takes me three to four months, to years, to actually make a move at that point. I think everything should be studied, and worried about a lot, before anything actually happens.

Are you ever afraid that you'll fall into the friend zone if you wait that long?
Oh, yeah, it always falls into a friend zone. That's definitely a concern.

What are some of your turn-ons and turn-offs?
I'm really talkative, which I think can be both a turn-on and a turn-off, but in terms of being a really good listener and being someone who can also respond to whatever you say with some sort of comment, I feel like that puts me slightly above the level of a kind of grunting, masculine jerk. Slightly above. But in terms of turn-offs, I'm really really anxious often, and stressed, and I have difficulty being the confident person who lurks within, or at least showing that.

So, this person that lurks within, does he come out in the bedroom?
Oh, absolutely. And once I get in there, everything's fine. It's just a question of getting from the library to the bedroom. It seems like a much longer walk.

Do women flirt with you? Can you pick up on that easily?
I think I usually pick up on it, and then I get — not self-conscious — but, I can't respond in the moment. I think the most pleasure I have is in telling friends the stories of situations that I was never able to close on. Last week, I was a bar with a girl, sitting on a couch with her completely alone, and she turned to me and said, "You know, sometimes I just feel like I want to be attacked by a man." And then I kind of touched her arm really, really gently, very, very nervously, and then she left.

So you didn't close the deal?
Absolutely not. And then my friends tried to hook me up with her a second time, and nothing happened the second time. I loved telling that story to my three or four friends, because they basically predicted, "What happened when she said she wanted to be attacked? Did you just kind of inch towards her really, really slowly?" And I'm like, "How do you know me so well?"