Nerve asks deeply personal questions to people we just met.
How would you describe the dating scene in Boston?
I've dated quite a few people, but I've never had a serious boyfriend in Boston. But, I've met them at anywhere from a birthday party to Relay for Life to Martha's Vineyard. And I've been on dates, but also gone places to do overnights way too quickly. There's a preppy theme here in Boston, and then blue-collar. I've tried both.
Any weird/embarrassing/off the wall sex experiences you're willing to share with the world?
Oh yeah. One guy asked me at the end of the date if I wanted to split it, which was mortifying. And then the sex was really bad that night and I could not get into it. And he got annoyed with me — we'd only been seeing each other about a month and a half. He got really irritated and then just rolled over and went to bed. So that was awful. But then, with this other guy… so, I have orgasms from everything else, but never from sex alone, and I had my first with him twice in the same sex session! It was so exciting. Best sexual experience of my life, by far. There was another guy, though, who must have had a premature-ejaculation problem, because both times I hooked up with him, he came within thirty seconds. So that was uncomfortable. He apologized, and I tried to make it okay, like "Don't worry about it! Why would you wait? Orgasms are fun!" but I think it was a deep-rooted problem for him. No complete horror stories though.
That's good. What are you looking for in a partner?
Right now, short-term, intense lust. Excited about each other, close communication. I'm a serial monogamist, so that's what I'm looking for. Two month stints, four months tops. Nothing less than two months though — then I feel cheap.
So, how do you know when you meet someone that you want to be with them? What about them attracts you?
Well, sometimes it's just an instant sexual attraction. Actually, it's usually just that, to be honest. If they're not too nice, not too mean, then I like them.
Do you believe in love at first sight?
Yeah, I guess so. I've never had it. I've never been in love — I said it once, but I wasn't. They made me say it. After a few months of just saying, "Thank you," I had to start saying it. But I do believe that maybe you could love someone at first sight. What I don't believe is there's one person for everyone and that you marry the first person you fall in love with. There's maybe 1200 people for everyone… probably closer to 1200 in the whole world. So you're probably going to have love at first sight happen in your life, but you shouldn't marry them. You should be in love with them for two to four months. No, I'm just kidding. Maybe a year if you love them. Then move on to the next. A year is a definite breaking point. I've had two year-long relationships and always at a year is the time where I decide, "Do I want to proceed or do I want to snip?" That's when you snip. If you're not sure, you snip. If you're not in love after a year, you snip.
Snip snip, got it. Kinkiest thing you've ever done?
Never had a threesome, never been with a woman, never had butt sex. Considered it, never got the courage to do it. Never had a vibrator. Have a vibrating ring from sex, which I kept, but it's not the real deal. Never had sex with two guys in the same day or week. Month, yes.
NEXT: "I find the men in Boston much more chivalrous and manly, and I like that…"
So, you just moved to Boston?
I'm from L.A., but I moved to Boston this past April for work.
Can you compare the West Coast/East Coast dating experiences that you've had? Have you noticed anything about the dating culture or the men/women that you're interested in?
I've dated a bit here, and I think it's easier to date here than it is in LA. I think people are more outwardly friendly there, but you're not really sure what you're getting — whether it's superficial or not. Whereas in Boston, I don't think people approach you unless they really want to approach you. I haven't dated too much in Boston, obviously — I've only been here for about five months — but I think dating in LA is very aggressive. It's hard to describe, but I think there are a lot more women to men in LA, and men know that, so they can be picky for whatever particular reason they want to be and just move on to the next person. And I've had friends in LA who are from Boston, and it seems relationships with those people last longer than those from LA.
Interesting. Now, with the people you've been out with, can you tell us about any good dates, bad dates…
I should preface this by saying that I'm a horrible dater. I'm a very long-term relationship person. Dating, I suck at. I've tried online dating in LA, and I also suck at that because it's like a second job and I don't have the time for it. I find the men in Boston much more chivalrous and manly, and I like that. As opposed to the men — I'm bashing my hometown so much — in LA, where they're much more metrosexual. They probably put more time into their appearance than I do. Hollywood rubs off a lot on LA, but the chivalry isn't there as much. Most of the guys who I dated on the West Coast ended up being from the East Coast most of the time. The dates that were good were with men who tended to be from the East Coast. I've only dated one guy here, but he was very chivalrous and old-fashioned, and I liked that.
Since you say you're mainly in long-term relationships, what attracts you to those people? What makes you decide to be with them?
It just fits and then it gets — and this is not necessarily always a good thing — it feels comfortable. There's no more awkwardness. You just know it's right.
Do you believe in love at first sight?
I don't believe in love at first sight, but I do believe in a strong attraction at first sight. A connection.
Have you experienced that?
Yes. More than once. But I think it changes as you get older. The first time, it actually worked out. After that, not so much.
And what are you looking for in a partner?
Loyalty, honesty — those are the two key things. That was really difficult to find in LA — there's much more of a revolving door there in relationships, waiting to see what the next best thing is going to be.
Do you have any crazy exes?
Not anymore, thank God. I'm thirty. I did when I was younger, but I'm still good friends with most of my exes, so that's a good thing. I didn't do anything bad, and neither did they, so I still talk to most of them.
NEXT: "I'm never going to tell her, because one of the girls was her roommate…"
Does being a waiter get you any dates?
Um, nope. I've only been working a few months there, but I don't get any numbers or anything like that. Old ladies hit on me, which is kind of weird. Tell me I look like Todd English or Rick Fox. Most of the time it's not even my table. They just call me over from across the room.
Tell me about a weird or fun dating experience here in Boston.
I met this one girl through my friends and took her on a date and ended up having sex with her.
Yes? And… was this fun? Or weird?
It was fun and weird. Just took her out and ended up having sex with her in my car. It was cool. I just got of college so, that was great, except I had to fucking pay for everything. It's expensive. But it did pay off. I'm really lax in dating. I just haven't been a big dater. I dated this girl in college, but still had sex with other girls just because I could. She still doesn't know. She just texted me actually. I feel bad. But I'm never going to tell her, because one of the girls was her roommate. Her whole group of her friends would break up. It'd be really bad.
You had sex with her roommate? While they were roommates together? How did that happen?
They all went to a club, but this girl stayed behind — it was during spring break — and she just called me and asked me to come over. She started it, not me. It was fucked up, but the girl who I was dating was pissing me off. She was down at this club, not answering my texts…
So you fucked her roommate.
Yeah, it was really stupid.
And do you see yourself dating her monogamously now? Now that you're exchanging texts again?
Maybe. Just 'cause there's so many fewer girls around. In college, it's like a free for all. Girls are wasted every night, being idiots. And now, you really have to try. You have to take girls on dates and stuff. It sucks.
So you prefer the former lifestyle?
Eh, it started taking a toll on me. I just started feeling really stupid at the end of college. Braindead from all the drinking and smoking and partying. So I'm glad I took a break. But I don't really get girls. I just go with it. A lot of the time it happens to me, I don't have to do anything.
What's the craziest thing you've done to get laid?
I don't know. I did a lot of dumb shit. I used to drive drunk, pick girls up. I don't think I've done crazy things to get laid, but I've definitely had sex at weird times in inappropriate places.
You'll think I'm such an asshole. Well, it was at our first "day drink" at school — a Saturday where everyone wakes up and gets shitfaced — and this girl and I were just drinking and she goes, her words, "You want to go upstairs and have a quickie?" And I was sitting there taking a shot, thought she was joking, and then she was like, "Seriously," grabbed me and took me upstairs and I had sex with her at around eleven in the morning. And then right after that, I got a call from this other girl who I was hooking up with and she asked me to come over and have sex so I did. That was one in the afternoon. And then the girl I was kind of dating met up with me at around seven in the evening, and we had sex. And then this girl I used to hook up with called, and I went over around two a.m. and had sex with her.
There are only so many hours in a day! Four different women in one day!
Yeah, you've got to shower in between. It was pretty aggressive.
That's more than pretty aggressive!
I'd say three of them, I didn't even initiate it. Just kept it going, I guess. I was shitfaced all day.
Huh. Well, I was going to ask what the kinkiest thing you've ever done is, but…
I haven't really done any weird stuff. I've only had anal sex one time in my entire life. I don't even know who initiated it.