Love & Sex

Talking to Strangers: New York

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“What’s the craziest sex you’ve ever had?” “Two girls in a phone box. ”

Emily, 26

Where are you from?

I’m from Detroit. The dating scene here in New York is really different. I feel like men in Detroit are really fun, but they’re very immature in comparison to New York men. I feel like men in New York City, while they’re more mature in their careers and their aspirations, the purpose for them being here is that they’re after their goals and their dreams, so dating them is kind of like being second in command. 

In Detroit, you get that Midwest mentality – you want to be married around 27 or 28 and it’s kind of ingrained into you that you should have yourself established by that point – and you get a lot of immaturity with it. I feel like there’s a screw loose or something because I don’t want to get married until I’m like 30. I guess at home the mentality is whether or not you’re ready for it, you’re just sort of diving in. Here everyone’s a little more free to move at their own pace depending on what their culture, background, and financial status are, whereas back home everyone’s like fuck, I’m 27, what the hell am I doing with my life?

Does your job ever get you laid?

I’m a waitress at this bar, as well as a portrait photographer, and being a waitress gets me more laid than being a photographer. I’ve been working there a couple years, you meet a lot of really cute guys. I’ve hooked up in the bathroom, not with a customer though. And I’ve kind of been dating one of my coworkers for the last couple of years. We did meet at work. 

Do you have any plans for Valentine’s Day?

Not this year. What I intended to do is hang out with my roommate and order a pizza, but who knows. 

Do you have any bad breakup stories?

I was with this guy for about 3 years and we broke up a few different times before the relationship was finally on its way out. The first time he broke up with me in a Dairy Queen parking lot. He made me pick him up, and before I knew we were gonna break up, I’d picked up a pizza. On the way home he dared to ask me, “Can I have a slice of that?” What a dick. And the second time we broke up was on the day of my brother’s high school graduation. Obviously he was not the one for me. 

Did you learn anything from that relationship?

Stay single until you meet someone who makes you a better you. It’s as simple as that. You meet a lot of people in New York City. You meet travelers, you meet people who are just here on temporary jobs, and there’s a lot of different people with different standards of dating. If you’re gonna commit yourself to someone, wait for someone who really enhances you as a person. 

What’s the worst sex you’ve ever had?

Probably when I had sex with a guy who was a profuse sweater. That’s all that needs to be said. It was pretty gross. 

Jameson, 25

So you’re a film editor, does your job ever get you laid?

God no, all my coworkers are fucking creepy. But I did go out with one of my old coworkers the other day. He took me out to see Sleep No More, it was amazing, he paid for my ticket, it was incredible. But nothing sexual happened, he didn’t even hold my hand. A few days later he was texting and asking me to hang out, but I didn’t want to see him, so he said “I guess I’ll go hang out with my gimp friend,” and I say “Oh, like S&M? I didn’t know that about you, but nice job just throwing it out there out of nowhere.” 

Then he started telling me how since his divorce six months ago he’s started being more experimental, but he hadn’t been that experimental…yet. So I start thinking about what exactly he’s insinuating. Me as a gimp, or him as a gimp, and I don’t really know him well enough for that shit, not that there’s anything wrong with that, but he and I hadn’t even kissed!

What’s the worst sex you’ve ever had?

He used my shoulder as a bed frame and dislocated my collarbone. I couldn’t fix it until almost two weeks later, when I turned in my swivel chair at work too quickly and it popped back in. I did not want to go to the doctor for that, and that was really stupid because now I don’t think it’s in the right spot. So that’s a permanent sex injury. I didn’t tell him when it happened though. In the morning I had to get him out of my apartment and he asked me where the closest CitiBike was to get back to Bushwick, and all I could think was oh my god, are you kidding? Why are you even talking to me right now?  

Do you have any dating tips?

Do what the fuck you want to. Don’t do that whole wait two hours to text back thing. Just fucking do what you want. If he’s the right guy it’ll work out, if he’s not right then it won’t. And you will not fall in love in New York because it’s impossible. There are so many really beautiful intelligent women who are in their late 30s, early 40s, who have dated incredible guys, and no one wants to settle down. 

What’s your best/worst morning after story?

I hate the home field advantage, I usually leave at 5am. A guy will know that I’m serious about him because after a few months I’ll actually still be there in the morning. One of the first guys that happened with was this guy I was seeing when I was living in Seattle when I was 22. When he woke up and I was still there, it was a huge deal to him. This guy would never stay at my place because I had six guy roommates and he was afraid of all of them. But he lived in a studio, and his dad was actually on his floor in a sleeping bag because his dad was homeless at the time, so we usually had sex in the bathroom.

But the first time I stayed there we were drunk and hooked up on the couch just feet away from his dad, which was really fucked up. In the morning his dad and I went to work at the same time, but he was so nice and made me a smoothie and gave me the best apple there ever was. It’s Washington State, and he gave me this apple that tasted like magic, so every time I’d go over I’d tell him how he gave me the best apple ever and that’s all we talked about for the next three months.


Seán, 28

Does working as bartender ever get you laid?

It’s easy to get laid doing this. The weirdest one actually happened a few weeks ago. A girl just walked in right before close, she wasn’t even drunk, and she just gave me her number and told me to follow her home. She only lived two blocks away. She was older than me, about 40, but she was hot. And I had to leave her house very early the next day. Younger girls know how to get fucked, older women know how to fuck. 

What’s the worst sex you’ve ever had?

It was weird, I was having sex for only about 30 seconds and the girl just sprayed all over me. And then she wouldn’t let me fuck her anymore. I literally put my dick in her for 30 seconds and that was the end. I thought she was pissing at first, but she wasn’t. The best sex I’ve ever had was definitely on holiday two years ago, but that’s all I can say, because if it ever gets out my ex-girlfriend will kill me. My ex was the best sex I’ve ever had ever, though. Just the best. I still talk to her, but it’s over. She’s the only real girlfriend I ever had, and I dealt with her for five years. She was the one. And now she’s gone. But after five years everything happened, so that’s that. 

Angela, 21

What do you do?

I’m a student and I bartend. And my job does get me laid. I’ve probably had sex with 3 or 4 customers. I met my boyfriend there, and now we’re gonna live together, so that’s a good story. He was sitting at a table and I was behind the bar and we were eye fucking all night and then he walked out and then he came back in like 30 seconds later saying I can’t leave without getting any of your information and thats how it started. It’s cute, right? 

Do you have any Valentine’s Day plans?

We’re getting a hotel and having crazy hotel sex and then the 15th we’re gonna go to The Russian Tea Room. Very fancy, I’m excited. 

What’s one of your craziest hookup stories?

I’d have to say the craziest was probably waking up in Brooklyn having no idea how I got there or where I was. But that may have been date rape. I don’t know if that’s funny, I’m sorry. Mostly just late nights on a variety of different drugs. 

Do you have any dating dealbreakers? 

Hypocrites. Too eager, thirsty people, you know what I mean? When it’s like, I know you like me and I like you but don’t act like you like me that much, it’s so gross. And to be honest, girls pretend like they’re not shallow but they are. If a guy is good looking it automatically gets rid of whatever dealbreakers basically, except obviously no cheaters. I haven’t been cheated on that I know if, but I feel like I probably have been and they just didn’t say anything. I’ve cheated on people twice and I hated myself for it both times. I broke up with the guys I was seeing immediately after both times I did it. I told them why, I didn’t like myself for doing that to them.

How many people have you slept with?

I can’t say a definite number, because I try not to count, but at least 35 or 40. Every guy is like “Oh, my ex-girlfriend said she only slept with six guys,” and I’m like no girl in New York City has only slept with six guys. Maybe these past few months. My boyfriend knows though, we’ve talked about all those sexual things. That’s the only guy I’ve ever told that to, or ever would tell, because we’re completely open. 

We’re considering having another guy join our sexual thing. We’re in a dominant/submissive relationship, I’m the submissive one. But I’m not comfortable with other girls sexually. It’s just not my thing. But he’s interested in sharing me, so we were talking about that. So once he moves down here in April we’re gonna start the process of finding a third party to join us on the reg. It’s not going to be an every time thing. We’ve been together since about Thanksgiving. He’s living in Massachusetts now, and to keep up with the long distance thing I suggest lots of sexting and naked video chats. I feel like that’s a big thing. I feel like the reason why a lot of marriages and relationships fall apart is because other people become greedy or unwilling to do stuff that they don’t like that will make the other person happy. 

Any other sex tips?

I give really good blowjobs, but that’s just me. You can’t be afraid to go deep. And don’t be afraid of butts. Don’t be afraid of his butt, and don’t be afraid of your butt. You know, just be clean about it, and it could be a lot of fun if you’re doing it with the right person that you trust. With a lot of lube, a lot of patience and a lot of love it can be fun for all parties, men or women. 

Darren, 23

How does the dating scene in New York compare to Ireland, where you’re from?

I’ve been here eight months. In Ireland you stick to your own clique, here it’s broader. Bars are very cliquey, but over here it’s different. You meet everyone when you go out. I’ve been in a relationship for about five months, we met through friends. I asked her on a date two years ago, and then I went home. So when I saw her again I said we still have to go on that date. She didn’t think I was serious two years ago, she thought I was just drunk. 

Do you have any crazy exes?

My ex-boyfriend now has a girlfriend, and I also have a girlfriend. I was gay, or I thought I was, and now I’m straight. I don’t fancy any other fellas, it was just that one guy. He was my friend and he was a nutcase though. I used to have to calm him down and look after him when we were out, and that’s how we got together. We were together for two years. People didn’t believe we were together because we were friends before that they thought we were just still friends. It definitely wasn’t a big deal because we were still hanging out with the same people, we were just then a couple. People thought that we were fucking with everyone by saying we were together but we were. Still friends, though. But he has a girlfriend now in Ireland. He came over here to visit me and my girlfriend met him. She thinks he’s a nutcase as well. 

What’s the craziest sex you’ve ever had?

Two girls in a phone box. 

A phone box?! How did that happen?

I don’t fucking know. I got lucky. Another time I’d moved in with my friend, and we went out and pulled two friends and he had one girl and I had the other. So the next morning one girl called her friend into the room and they started having sex and doing stuff to each other, but I was just sitting there. I wasn’t allowed to get involved. But they were in my bed. I didn’t mind watching though. 

Do you have any sex advice?

Use your thumb instead of the other fingers. I don’t know why, but they like when you use your thumb. 

Alex, 22 

What do you do?

I’m a chef, I’ve been doing it since I was 16. There’s a lot of debauchery in the culinary underworld that most people don’t even know about. At one restaurant I worked at, this kinky waitress would flash me her stuff when I would go into the walk-in fridge during work hours. It was a pretty obvious sign. I took her up on the offer in that walk-in fridge, it was one of my prouder moments. The cold didn’t cause any problems at all. I was on my game. 

Do you have any plans for Valentine’s Day?

No, but that’s the best time to find a date though. I figure anyone out is single, so I’m gonna work that angle. 

Do you have any crazy exes?

Most of the time when I’m done talking to someone I’m just done with them. I just never talk to them again, whether they call or text me or not. It can get a little stalk-y, because I’m so unresponsive at times, but I take it pretty lightheartedly. They get the point fast enough. 

Women in New York are a breed of their own. I’m not from here, I’m from Cleveland, Ohio and it’s nothing like this. Dating in New York everyone’s more responsive, really. Everyone’s looking to meet people and make new friends. Back in Cleveland it’s not so much like that. You’ve got to get to know someone. There’s not a lot of casual sex going on there either. I prefer New York way better. 

Do you have a favorite sex position?

I like to do the least amount of work possible because I’m lazy. After a long day sometimes you just don’t have all that in you. 

Do you have any sex tips?

Learn how to cook. I cook for girls all the time. I don’t have a signature dish, but I’ll throw a lot of aphrodisiacs in there. A lot of red meat, red wine, avocado, stuff like that. And chocolate for dessert. Whatever the dessert is, it has to be chocolate. And I make breakfast the morning after.