Love & Sex

Talking to Strangers: New York, NY

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Nerve asks deeply personal questions to people we've just met.

Jena, 28

What's your occupation?
I'm a comedian.

What's a relationship dealbreaker for you for guys?
I never get to the relationship point, but just in dating, if a guy tries to have sex without a condom, that's a dealbreaker.

What is the kinkiest thing that has ever happened to you or that you have done to someone else?
Kinky is open to interpretation. I guess fooling around in a graveyard. I would have had sex, but it was a Jewish cemetery and I just didn't feel right about it.

Are you Jewish?

But if the cemetery was any other religious denomination –
Oh totally, yeah. I would have totally gone for it.

On what date number did you decide to go to the cemetery?
This was with my ex-boyfriend. We snuck into the cemetery.

Did you sneak in for the explicit purpose of fooling around in the cemetery?
I find that cemeteries are really fertile places because a lot of people take their dreams there to die. A lot of people don't live their dreams so they get buried with them. As a result, cemeteries are full of life and dreams. They're very erotic.

Why did you guys break up?
Because I moved to New York and he's in Chicago.

Are you single? Dating?
Dating. I know this is not 2005, but I started a blog called Not So Lonely Planet and it's a guide to men in other countries. Like the way Lonely Planet is a cultural roadmap, this is a roadmap on how to date men in different countries.

Are there any men you prefer based on their geographic location?
From my experiences, I really enjoyed hanging out with French men. German men kind of scare me. I do stand up comedy so I travel all around for comedy. I meet people and I go on dates and I capture those dates in this blog.

So what's so great about French men?
Well, German men are aggressive, and Italian men are insane. They'll be like "I love you" and it means "let's grab a cup of coffee." And this German guy I dated was so meticulous about us splitting drinks and the bill and stuff, and that was so unattractive. But the couple of French men I've hung out with seem like they know women. They're confident. They just know how to seduce women in an awesome way that doesn't seem creepy. They know how to seduce women in a way that's sexy. Not aggressive but just the right amount of aggression. Not too hot, not too cold.

Where do you recommend picking up these guys or getting picked up? After your shows?
I don't want to meet anyone who has seen me do comedy. If you're in a foreign country and you clearly don't look like you're from there, you will meet people. Men can smell that on you. You're like prey. In New York, it depends on what you want. If you want to be held by a stranger, go to a bar at 3 a.m. New York is a different breed. I have no advice on how to date men here.

Have you tried online dating before?
No. I just need to smell men's pheromones.

Do you have any general advice for guys?
When you have sex with a girl, wear condoms. A lot of my friends in New York have all had these experiences where really awesome, nice guys try to fuck us without condoms. If anything, it just shows you are not responsible. You are not responsible for your own shit.


Todd, 25

What's your occupation?
I work in children's cartoons. I draw the background for cartoons, like a cartoonist.

How did you lose your virginity?
Lost my virginity on prom night in high school. Classic way. I'd been dating the girl for a while… seven months?

How long did you two last afterwards?
Off and on for seven years.

Well, I'm not with her right now.

What's the kinkiest thing you've ever done? Or had done to you?
Butt play? I don't know.

You playing with her butt?
A little bit, yeah. A little digital manipulation.

Was it a request? Or an improv performance?
I think the worst thing would have been if it were an improv performance.

What's one thing you wish girls would do more of in bed? Or less of?
Oral sex. Going down on a guy should happen more often. At least in my experience, that'd be nice.

Do you care if it's a spit or swallow situation?
I don't care.

How long would you wait for sex?
You mean like, lose your virginity sex?

No, that only happens once. I mean like if it's like Date One, Two, Three, or Four… when does it become unreasonably long?
This is going to skew your responses. She's the only girl I've been with.

Yeah. Otherwise, I'd give different answers. I'm throwing you off here.

You are! Can I ask what happened to the relationship? Why didn't it work out after seven years?
She moved to Korea for a while. We're really bad at long-distance, so we decided to cut that off. Mutually.

And how long have you been broken up?
Eight months.

Are you actively dating? Or how do you plan on actively dating?
I would love to be actively dating. Right now, I'm just trying to go out and do more things that I like and then meet people who like doing the same things. And I'm on an online-dating site but it's not working out great. I just started.

So what's an online-dating dealbreaker? What's a 'delete'?
If you can't write coherent sentences, that's a dealbreaker.

Do you respond to girls who hit on you?
I'm all for girls hitting on the guy. That's fine. I have responded to that. I guess they didn't like my responses.

How many internet dates have you been on?
I only started a month ago.

So you haven't upgraded to the real-life experience.
No. I think if I said yes to some of the girls who messaged me, I would have gone on some bizarro dates.


Ashley, 25

What is your occupation?
I'm in grad school right now.

What's your relationship status right now?
I'm in a long-term relationship.

Do you have any advice for people who want to be in long-term relationships? How did you do it?
I don't know if I like that way of thinking about relationships. I think it's really good to be single, and I just somehow found myself in a long-term relationship. If you are desperately searching to be in a long-term relationship and it's not working out and you're frustrated, start by chilling out and being happy where you're at. Figure out what you want to do. And then just date a lot.

So what was so special about this guy?
He's got his shit together. I spent a lot of time dating guys who weren't as motivated or proactive about getting their life together as I was. I ended up taking care of them, and it's really important to be with someone who doesn't need taking care of. Having an equal relationship is an important thing.

How did you meet him?
We actually met online.

Did you have any dating-profile dealbreakers? Or internet-message dealbreakers?
Anybody who needed to be in a long-term relationship immediately — if they were looking for the person they were going to be with for the next five years — that was not someone I would be interested in. You have to be relaxed about it and not on a mission.

Do you have any general dating advice?
Mostly, don't settle. It goes equally both ways: don't settle. It's not a good mindset. If it's not working and if it's not really want you want, don't just assume there's nothing else out there.

On the sex front: any constructive criticism for guys? Or pet peeves?
This is a really predictable answer but confidence is really important. I think guys worry a lot about coming across as too aggressive sometimes. That they are going to be the asshole. But I think it's better to take the risk and be out there. Why not? Be upfront with people about what you want. When you first have sex with someone, you have this feeling-each-other-out thing going on. The best way out of that is really communicating what you want — that goes for both parties. Don't be shy about it. That's when things get awkward and uncomfortable. Be upfront and go for it! Obviously, respect people's boundaries.

Did you have any crazy dating stories from before this relationship?
Yeah. I've had horrible experiences where I was in a relationship and I needed to break up with them and they just wouldn't let me! I'd try to break up with them when we were at my apartment or their apartment or someplace private and they wouldn't let me leave. Then they'd break down into tears, and then I'd comfort them. Just emotional manipulation. And it's not okay, and it's hard to draw boundaries especially when you care about somebody. Are they being emotionally manipulative? Are they being vulnerable? How much of an asshole should I be in this situation? Ultimately, for everybody, it's better just to be the asshole.

Kip, 34

What do you do for a living?
I'm a bar manager.

Do you have dating advice for guys based in your experience in bars?
Don't be a douchebag. Like, if she's not into you, she's not into you. But also don't be afraid to talk to people. If you want to buy a girl a drink, buy it through the bartender. Be classy about it. You're going to have a lot more luck that way.

Any advice for girls based on working in a bar?
I feel like girls can do whatever they want in a bar but I think I would give similar advice to girls. Don't be afraid. If you're into somebody and you want to go talk to somebody, what do you have to lose? There's nothing to lose.

What is the kinkiest thing you have ever done or had done to you?
Kinkiest? I think that is so hard to answer because what might be kinky one day isn't necessarily kinky the next day. I think kinky has everything to do with how much fun you are having with the person you're with.

Can you give us an example of one moment?
Yeah, well, there was definitely 'The Toe Girl.'

'The Toe Girl'?
This girl just really liked toes. We can leave it at that.

Like you interacting with her toes or her interacting with your toes?
She liked interacting with my toes. Let's just say that toes took the place of fingers in a lot of ways.

Oh. Whoa. Okay. Do you have any relationship pet peeves or dealbreakers?
Intentional game playing. Fishing for things you want to hear is kind of a dealbreaker. When you are more concerned about yourself in a conversation than trying to hear what there is to hear, that's a little boring. I don't want to be your therapist. I want to be your boyfriend.

Is there any sex advice you 'd like to give to girls, aside from 'Toe Girl'? You can use this as your PSA right now.
Women: do not be afraid to let yourself go. Do not be afraid to be loud. Do not be afraid to say what you want because guys like that a lot. I think the same thing can be said for guys, too.


Willie, 27

What's your occupation?
I'm a sales associate at a retail store.

What's your relationship status right now?
I am single and loving it.

In a breakup, are you normally the dumper or the dumpee?
Normally, I am the dumpee.

Why do girls dump you?
I don't know. Most of my experience has been with long-term relationships, so it's like a long, drawn-out "okay, we're both tired of each other, let's stop this" sort of thing. It's not like there's any particular reason. It's just been a lot of being with someone for a long time, then being tired of it. It starts like, "we need to spend some time apart," and that time turns into all the time apart.

Are there any specific relationship or sex dealbreakers that you've experienced?
I generally try to cut that relationship off before it even starts. I'm pretty good at interviewing.

What is something that would turn you on? Romantically or physically.
Education is a really weird turn-on for me. I don't have a Master's degree and I really want a Master's degree. I guess I don't meet a lot of people who have higher degrees so I get really excited about it.

Are there any particular specialties you're interested in? Liberal arts vs. hard science?
Actually, science is really, really good. If it's a business Master's degree, I could care less about it.

That gives the nerds something to root for.
I know right? I love nerds.

What's the kinkiest thing you've ever done or had done to you?
Well, me and my girlfriend at the time decided to role-play a little bit. We did this really stupid plumber and person with a bad sink. I was the plumber. It basically turned into a porn: "Oh, I'm gonna fix your sink" and "oh, sorry, I didn't get dressed after the shower." It really just kept going on and on. We just kept spouting innuendo after innuendo at each other and we weren't really getting anywhere. And so we just stopped and had sex. I don't know if that's considered kinky or a weird thing that happened.

Whose place were you at?
We both lived together. It was odd. I guess it wasn't kinky though.

Were there any other scenarios you tried after that?
We pretty much figured out that we weren't really good at it.


Maya, 18

What's your occupation?
I'm a college student.

What's the best dating advice someone has ever given to you?
You should be with someone you enjoy being with and not someone who you see a future with. I find that I can get really ahead of myself. I got that advice from my mom.

And are your parents still together?
No. They are very divorced. [laughs]

So are you single or dating?
I currently have a boyfriend.

Can I ask how you guys met?
Yeah. There's this thing at my college called Safer Sex Night, which is essentially the Sexual Information Center's plan to get people to have safe sex. Everyone gets drunk and goes to this party naked. It's funded by the school and there are condoms thrown everywhere. So I went —

Well you have to cover your genitals and your nipples. Both genders. Those are the only guidelines. So I was wearing this mesh dragon suit and I went up to said-boyfriend who I barely knew. We both started dancing, and we were both really fucked-up, and I went back to his place, and we had really, really good sex. Afterwards, I stayed over and we were both saying sarcastic remarks. I was commenting on how bizarre the situation was to myself and all of a sudden I realized we were making each other laugh.

Was the intention for it to just be a hookup and then it got promoted?
Yeah. Essentially because we talked and that worked. We had sex and it was awesome! Then we stayed up the whole night joking. And then we thought we should date because we have sex and get along.

Wow. So you really took your mom's advice.
Yeah, I really did. And I've had to apply it to him. Because I've thought, "I don't know if we're going to get married." Then I realized it doesn't really matter because we have good sex. It's just my own neurosis of "Where is this going?" Then I remind myself that I'm having fun and I'm having a good time. We like each other and that helps.

Before dating this boyfriend, did you have any terrible dating or experiences?
Yeah. I had a crush on this boy who was two years older than me when I was in high school. Finally I was a senior and he was in college and we hooked up randomly. He's a very pretentious guy. Essentially right before we started hooking up, he was quoting Thoreau to me. Then while we were having sex, he was very vocal. He said things, like full sentences and phrases…

Can I ask for an example sentence?
Well, I had a really big crush on him. Then while we were having sex he said, "Is this just how you imagined it?" and I started to laugh. So I said "What?" And he said, "Well, did you imagine it just like this?" And I was like (sarcastic voice) "Yeah! Sure! In your bed!"

How was the sex?
Um, it was okay? Mediocre?

Just like you imagined it?
Just like I imagined it! And the next time I saw him I told him, "You're very vocal! I was actually surprised at how upfront you were."

And was there an encore?
No, just friendship.

I was just wondering if he had a chance to take on your constructive criticism.

Interviews and photography by Nancy Sun. Want to talk to strangers in your town? Email