Hooksexup asks deeply personal questions to people we just met.
Sasha, 31
What's your occupation?
I'm currently unemployed. Normally, I do operations and accounting and office stuff.
Have you ever gotten laid because of your job?
No, not that job, but I got really interesting dates out of my job when I worked for Waffle House. For Waffle House, not at Waffle House. I was in Human Resources, and guys come in. Attractive older men come in, and take you on dates on helicopters.
I'm sorry?
A guy asked me out. He was really charming. His friend was charming. I was probably twenty-three, and he was probably thirty-four. I said yes, and he picked me up and drove me in a Hummer to a little airport and took me on a helicopter ride. And then he flew us to Chateau Elan where we had dinner and wine, and then we flew around the city and that was it.
Do you have a thing for older men?
I think I did have a thing for older men. I think I have daddy issues, and I found comfort in dating an older man at a time in my life. But I started getting sick of how all the older men had so much baggage, and so many issues. They all had so much time to build up their issues. So I somehow started dating younger guys for a second.
When you say younger, do you mean younger than the older men, or younger than you?
Younger than me. That was terrible, too. [laughs] They're so cute and they're naive. You have to be intuitive and pay attention to the details and the interactions with a woman to know what the next step is. Younger guys don't have that at all. At all.
At what point do you think men and women figure that part out?
I don't what the dividing line is, but I'm thirty-one, and I'm loving my thirties. You know what you want in your thirties. You know what's bullshit, and what's worth your time, and what isn't.
What are some dealbreakers for you?
I remember a dealbreaker for me once was — and I feel like this sounds like a Seinfeld episode — but, a guy didn't say bless you to me. The first time, I called him out on it, and he thought I was crazy. And then the second time he did it, I sneezed and he didn't say anything, and I just saw there and I brewed and I brewed, and I didn't go out with him on a date after that. I have manners issues. I think when I was single, I tried to tell myself, "This is not a dealbreaker. This is silly," but now, if my husband didn't say, "Bless you," to me, I'd be pretty pissed.
Prior to being married, how did you approach guys?
I'm a big fan of the eye lock, and I definitely would never suggest approaching someone before you can make eye contact across the room, because then when you talk to them it's like [imitates trumpet fanfare]. It feels like there's a moment then, as opposed to a person just coming up to you. I think the most important thing is to look approachable. I swear, I see people all the time, and they look like they're smelling something bad. They just look unhappy. Nobody wants to talk to you if you're like that. And not even just you — if your friends are like that, then you're just as unapproachable, because you're surrounding yourself with these negative-looking people. Smile.
If there were a book written about your sex life, what would the title be and why?
Oh shit [laughs]. Trials and Errors. I've made so many mistakes. When I look back at my twenties, I feel bad for myself. I was just so starved for any sort of male attention. Almost like a child. And I compromised myself in so many ways. I always wanted to be the fun girl. I think it really does stem back to daddy issues and being an only child and my mother telling me that I was the most amazing thing on Earth and that no other love was every going to compare to that which my single mother could give me. I just had a really warped sense of what love was supposed to be like.
What's your definition of love now?
Love is home. It's where you feel comfortable. It's just where you feel at ease in yourself. That's the thing — when I look back at my early twenties, I wasn't really me. I didn't even know who I was. And I really thought I was looking for it, but I wasn't. I was conforming to this or that. I was a chameleon to the people around me. My husband was the person that helped me find out who I really am as a person. And I actually really like that person — I think she's pretty cool. [laughs]
Alfred Khalil, 31
What do you do?
I'm an executive assistant.
Has your job ever gotten you any dates, or gotten you laid?
Absolutely not. It's not about what you do nowadays — it's how you look, what subculture you belong to, that gets you laid. My spectrum of what I like is vast. I think I look for how a person carries themselves — if they show confidence, personality. If they're funny, that's really sexy.
Where do you go to meet people?
There are really no places specifically to go. You can go the whole club route, but any stereotype you've ever heard about meeting someone in a club setting… a lot of people are extremely intoxicated, and some of them are there just looking for someone to have for that night. You can go to a neighborhood bar or restaurant, and the odds of you meeting someone of quality have been upped a little.
How do you approach people?
Me, personally, I don't approach. I've found in the past when I approached, maybe the guy isn't gay, or maybe he's taken off guard and made uncomfortable, because it's such an aggressive move for someone like me. And when I say someone like me, I mean that a lot of people tend to think I'm too attractive to do something as bold as that. Nowadays, I tend to act like I'm having a good time, either by myself or whomever I'm with, and if they're interested, then they're really going to have to approach me.
Do you judge a lover by his cover?
That's a tricky thing, especially in the gay community, because so many guys have had to act their whole life. They've had to put up some kind of front about their sexuality, and in a lot of cases that acting can carry over into the gay world. Who they are on the outside is not really who they are on the inside, or behind closed doors. Maybe a guy wears a shirt and tie forty hours of the week, and he's extremely masculine, but on the weekends, he goes out in drag. Running into someone like that, if you met the guy in a suit first and you were totally attracted to that, you'd be in for a big surprise. And for me, that would be a total turn-off, because I want what was presented to me.
What's the craziest thing you've ever done to get laid?
Maybe just totally expressed what I want in the form of a text message, versus insinuating. Actually, it was via Facebook.
If there were a book written about your sex life, what would the title be and why?
Being Gay Sucks. [laughs] I think it's harder for a gay man to find a meaningful and long-term relationship.
Ruby, 35
What's your occupation?
Artist. I do illustrations and fine art murals.
Has your job ever gotten you laid or gotten you a good date?
[Laughs] Nooo. I'm married.
Oh, well, that will certainly do it. How did you and your husband meet up?
At a bar. He hit on me. He actually stole my ID from behind the counter where I had it stored, and ran up to me and asked me if my name was Ruby or Nicole, because he wasn't sure if it was the first or the middle name, and I was just kind of like, "Who the hell is this guy and why does he know my name?"
And what about him turned you on?
Well, it was fetish night at the bar, and he was dressed as The Crow. He said I didn't have on enough eye makeup, and he asked if he could put some on me. So he did, and he kissed me while he was putting on the eyeliner.
Forward! Okay, what are your turn-ons and turn-offs?
Turn-on: I love having my toes sucked. That's my favorite. Turn-off: too much pain. I like a little bit; too much, and I'm done. If you spank me too hard or bite my nipple too hard, I'm done.
Where's the craziest place you've ever had sex?
I used to have sex on the roof all the time when I lived in this apartment building, and there was a skyscraper that was right behind us, so we always knew somebody was watching. I mean, out of the 500 apartments looking at you, somebody was looking.
You're pretty open about sex.
My parents are very conservative Christians, but my grandfather was very into Playboy, so I experienced Playboy at a very young age — when I was about four or five — because I used to find his copies. I thought the women were hot. They were sexy, and I guess I wanted to feel that way.
Have you ever hooked up with women?
Yes. It's just as good. Boobs! I like boobs. Nice boobs. Like, boobs that are good for the body. I don't want her to look like a boy, but they don't have to be ginormous. I worked at strip club for a while as a cocktail waitress, and I got to experience the real versus fake. If they're good fakes, and you can still feel the breast, then that's fine, but when it's hard and lumpy, it doesn't feel good.
What was that job like?
I tried to stay out of the drama, but it was a lot of fun getting to work there. I would never trade the experience for the world. I learned how women worked, and I learned how men worked.
How would you contrast how each sex worked?
There's a difference in men. I more enjoyed the men who were there for the companionship of the women and treated them with respect, rather than the ones that were like, "Bend over and show us!" Some of the girls had kids, and were completely normal outside of work, whereas some of them weren't, and so there was this big difference on levels of thinking, and actually, the ones who had kids and had normal lives and were normal people, were kind of more real.
Have you ever considered being a sex worker? What do you think the pros and cons of that would be?
Pros: getting paid to do what you like. [Laughs] Cons: disease. Getting in trouble. Getting in a situation that you couldn't get out of. But I do know some sex workers. That community attracts all kinds of different people. They're more accepting of everybody. Just this past summer, I recently hung out with quite a few and enjoyed their company. They're real people, and you wouldn't go, "That woman is a prostitute," but that's what they do. And I'm talking about men and women.
If you had to write a book about your sex life, what would the title be?
I'm actually about to write some pirate-themed sex novels. There's a huge fetish movement, but in addition to that, people just seem to like pirates.
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?"
