Talking to Strangers: White Plains, NY

Hooksexup asks deeply personal questions to people we just met.

By Grace Bello

Jamie, 28

What do you do?
I run a lumber company.

Cool. Do you meet a lot of guys that way?
Not ones that I date. [laughs] I'm recently out of a long-term relationship. We were together for four-and-a-half years. It ended about six months ago.

What was he like?
I met him through a mutual friend. It was great at first. It went downhill very quickly, and we tried to fix it, but it just didn't work out. We had the same interests, same background. We were from the same area, so we did a lot of the same things: hunting, a lot of sports, outdoor things, skiing. We were in the same sort of business. He did landscaping; I run a lumber company. Kind of a blue-collar boy, a little roughneck.

Is that your type, more or less?
Yeah, pretty much: big, brawny, roughneck guys. Truck drivers! [laughs] A lot of backwoods, down-home guys. A lot of dirty jobs. I like living here now because it's new for me, and I've been meeting a lot of different people. But back home, they're dirty all the time, they're muddy, they're loud... it's a different breed of guy. A lot of bikers, a lot of truckers. It's rough. You've got to be kind of tough. It's a rural area, where I'm from. There were probably about 10,000 people in my town.

What's the last great date that you went on?
Actually, I had a really great weekend. The other day, I went out with a friend of mine who I'm seeing on and off. Nothing serious, but we went away for the weekend. We went skiing. So that was fun. We rented a cabin. We had a really good time. Some friends, some family. We did a few things on our own. We went to the bar, went dancing. Some line dancing, like a real country girl. I'm very family-oriented; right now, I'm here at a bar with my sister! I go out with my sister and my family, so a guy who spends time with me and my family — that's big.

Do you have any dealbreakers?
Yes. If they don't want to have kids, then I don't want to be with him.

What if he already had kids with someone else?
Oh, that's no problem. I've dated a lot of guys with kids. I love kids; I think they're great. I'd rather have my own, but what're you going to do?

What was it like dating someone with kids? I've never done that. 
It's tough to leave. Once you know the relationship is over, it's tough to leave. You have a tough time disassociating yourself from that other person because of the connection you have with the children. And you know you're not going to see the kids, so it's even harder on you. So it's an emotional strain.

Did you have to sit down and talk with the kids and say, "I'm not going to be around?"
Yup. Yeah, I did. They were pretty heartbroken. It was hard on me. But you've got to do the right thing. You can't stay in a relationship to be with the children. I just tried to let them know that it wasn't their fault, they're great, and I love them very much, and things happen with grown-ups, and there's not much you can do about it. And if they wanted to contact me in the future — I always told my ex that if the kids wanted to talk to me, they're more than welcome to. I try to let myself be available for them if they need me.

Have you had any terrible dates?
The difference is, where I'm from, you don't really "date" that much. When you start seeing someone, you go out with them, and then it becomes serious. It's only an hour from here to where I'm from, but it's a totally different society.

Is it weird for you dating the guys here, who are more urban and possibly more sophisticated than the guys you grew up with?
It's not that these guys that I was dating up north weren't sophisticated. They just knew what they wanted, and they got it. Their fathers did it, and their fathers' fathers did it. Around here, it's a little different. People have families that they've strayed away from. Sometimes people down here don't have strict family ties. I've had fun with some guys out here, but I'm not really attracted to them. Not my type. I find them to be a little more about themselves than they should be. Guys up north, they're a little more oriented towards what they can do to make things better and how they're going to work things out. Things don't come as fast or as easy as they do down here. It's more work; you've got to work as a team. Not so much "I have this job, and you don't." The guys here are a little soft.

Kristopher, 25

What do you do?
I work in film and photography.

Do you get a lot of dates that way?
I do meet a lot of people, and women are interested in what I do.

What kinds of women do you meet through film?
You know, it's all different types really. I don't know what it is. Some say it's the way I look, the way I dress. I do meet a lot of women, and it seems like they want to get with me more than I want to get with them. I don't really get with women unless I feel a connection with them. I kind of stay laid-back with it, and it makes them insane — it makes them want to jump on me even more when I do that. I try to keep it civil and let them know that I'm just trying to be friends. In this business, if you just keep sleeping around, it's going to catch up with you. It really does.

So what's your relationship status now?
Single. A heartbroken single, but single.

Why "heartbroken?"
My ex broke up with me about six months ago. She lived in Germany, I lived in New York, so it didn't work out. She did it over Skype. Fucking Skype! It sucked. But I've been through it before. And I'm actually kind of glad. I didn't realize how much time and energy I was putting into it until after. And now that I realize it, I wouldn't be able to do all the stuff I'm doing now while having a relationship. Especially with her on another continent.

How long was the relationship?
It was about a year. I'd fly back and forth from New York, she'd fly back and forth from Germany. It was a lot of fun. I think now it was lust more than love, but there was definitely something cool there. Her spirit was really awesome. She was beautiful and kind and understanding of what I did for a living. She wasn't really the jealous type. It was nice all around, actually, now that I think about it.

Do you have any dealbreakers when you're dating?
If they look good, they dress good, and they seem kind, I start off with that. And then if they kiss well and get my blood going, it just progresses from there. I've been turned off by women who don't know how to kiss. I'm like, "Ugh, what are you doing?" How I feel around the person is what interests me.

Have you ever dated a virgin? They don't know how to do anything.
I did. My first real relationship — we dated for three and a half years — she was a virgin. She was awesome, great. She went off to college. It sucked, but what can you do?

Would you be intimidated if a woman had more sexual experience than you?
No, I'd actually be really excited.

Any awesome hookup stories?
I used to work at this tattoo shop. One time, this girl came in. I thought she was awesome. She came in, got a tattoo from someone else, and I just loved everything about her. Her attitude and everything, it kind of caught my eye. But I was so busy that I didn't have a chance to converse with her. So she left, and the other guy who had been tattooing her said, "She was feeling you, bro. Why didn't you talk to her?" I went outside to smoke a cigarette, and she was gone. But then my other boy, who was also tattooing, came out with the phone and said, "Here, some girl for you." I was like, "Really? Hello?" She was like, "Hi, I'm Emily. I was just in the tattoo shop, and I think you're really cute." So we ended up hanging out that night, and we hooked up. We ended up going out for, like, six months. It was definitely an interesting case of a woman stepping forward. That was cool.

Did you do any of the actual tattooing, or did you just help out?
I used to do tattooing, late-night shift. I was an apprentice at the shop. Now I actually just work in film. I do tattoo on the side, every once in a while if they're a friend of mine. But I wasn't like any of the other guys. They're awesome at what they do. Seriously. Some of their work is nuts. I can't believe I got their work at the price I got it at.

Did you ever have to tattoo any weird places?
I did have to tattoo a girl's vagina area. She wanted a smiley face. I was like, "Can we do a little tongue sticking out?" She said yeah, so I did a little smiley face with a tongue. That was definitely the craziest one I've done.

Kim, 31

What do you do?
I'm an executive assistant.

What's your relationship status?
I'm dating. He and I are both a part of the same sport league — roller derby.

What's that like?
It's amazing. It's crazy fun. It's a really great time. I got into roller derby in 2007. I've been playing for five years.

That's the one where you're roller skating and you're trying to bash each other?
Yup, full-contact sport, all on skates. It's offense and defense at the same time.

Is it easy to meet guys that way, or is it all girls?
I've met a lot of guys who were fans. My boyfriend joined as a referee, and we were just friends for a long time, and then we started dating. We've been dating for almost eight months.

What attracted you to him?
He was quiet, which was very different for me. But he kept track of little details. He'd remember things from conversations that we had that I didn't think were relevant, but he would reference it again in a joke. Of course, he was handsome. [whispers] He's sitting right there. We had a good time together. And roller derby is a hobby that's not based on your financial status or who you know, so when you meet them, it's based on just the love of the sport. Not all that "what kind of car do you drive?" and "how much money do you make?" It's kind of refreshing.

Do you ever get hurt during roller derby?
All the time. I'm covered in bruises every minute. I've been stopped in the grocery store by very nice women who have asked me if I'm in "a bad situation." And I've had to explain, "No, I'm not in an abusive relationship. I just play a full-contact sport, and I bruise easily."

Good for them for asking.
I know. That was really nice.

What was the last great date you went on?
I was taken to my very first Albany Devils game up in Albany, New York. That was a really good time. I was going out with my boyfriend and his father on a tradition that was always their tradition. So to be invited in on that was pretty special. We had a great time, and I learned all about hockey; now, I can be a fan because I understand the game. And I'm sure many more great dates will come.

Would you be able to go out with someone who wasn't a sports fan?
I don't think so. I love watching different sports, so if it's someone who has zero involvement in any sport, I think it would be a language barrier; I don't know what we would discuss. That might be a dealbreaker.

Have you ever had any bad dates at a game?
In the past, I've had bad dates where an ex was so involved in the game that I felt like, "Why did I even bother coming? I'm just sitting here on my own." Great dates are where you go to something you don't fully understand, and your date wants to tell you about it and explain why they love it so much. Then it's something for you to be involved in with them, and you share it. And that's a great date.

So you recommend sports as a good first- or second-date activity?
I think that you should do something where you're going to learn about the other person. Going to the movies, sitting in the dark for three hours, is not a date, because you're not really learning anything about the person. Sometimes going to dinner can be a little intimidating because there's nothing but conversation. So going to a sporting event where you can ask questions makes it so much easier. Then if it's terrible, you can just watch the game and enjoy it instead of being focused on this horrendous date.

What do you think is sexy about dating a fellow sports fan?
The different perspective that they bring. I have a ton of friends that are Yankees fans, but my boyfriend is a Red Sox fan, and that's a difficult thing to deal with in New York. You could be hunted down for being a Red Sox fan in New York. But something that's attractive about him is that he likes the team, he supports them, he doesn't back down with the opposing fans, and he doesn't hide the fact that that's the team he enjoys. That's admirable.