Hooksexup asks deeply personal questions to people we just met.
Sarah, 28
What do you do for a living?
I’m a waitress.
Does your job get you laid?
Yes. Not only do I get it on with random customers but also with some staff members.
Such as?
I've hooked up with a few bartenders and one of the waitresses. I’m not normally into hooking up with girls, except for every once and awhile. But I always want her to be the one to go down on me — I don’t do that shit. I feel like, if she’s pleasuring me, I’m still not really a member of that club.
If you had to pick one of the seven deadly sins to define you, which would it be?
Lust.
Why?
Because I’m lustful. If I see a hot guy — or girl — I point at them and say, “What’s up.” Give them a little head nod. Then I make him come over and do the work. I just give off that initial move.
What’s your most attractive quality?
Either my tits or my legs. I also have a pretty good sense of humor.
If you could sum up your first time in one word, what would it be?
Disastrous.
What’s your favorite sex position?
I’m a big fan of doggie. But I also like reverse cowgirl. That’s how I get off.
Do you have any dating dealbreakers?
Bad teeth — like busted, nasty teeth. Yellow or crooked. He’s got to have nice teeth. If I look at your mouth and want to barf, how am I going to hook up with you? Oh, and a big dick. I need a big dick.
Michael, 29
What do you do for a living?
I’m a lawyer, commercial litigation and criminal defense.
Does that get you laid?
Women are generally impressed by lawyers based on the age-old axiom that they're educated and financially stable. Also, the criminal defense side provides some amusing stories that can deceive a girl into thinking I'm witty, at least long enough for me to get her home.
Which of the seven deadly sins best defines you?
I like to think I'm a sick amalgam of pride, lust, and envy. I call it “pluvy.”
Do you have any sexual regrets?
Everyone has sexual regrets. I’ve slept with people who I shouldn't have. I've definitely slept with people I had no intention of dating, and having to explain that to them was almost never worth the encounter. More than anything, I regret all the girls who smiled at me on the subway or in a bar who I never approached and engaged.
What's your deepest, darkest fantasy?
Deepest and darkest? Is that like sex at the bottom of the ocean or in space? In a fantasy world, I'd have a harem at my disposal, ready to satisfy my every desire. Minus the eunuch, of course. Those guys freak me out.
What's your most attractive quality?
It's either my sense of humor or my forearms.
What's your favorite sex position?
I'm not sure I could explain it. A demonstration would be more appropriate.
Do you have any dating dealbreakers?
I have tons of dating dealbreakers. I think the main one is talking about astrology like it’s based in science. It’s an entirely fictional discipline made up to con the naive and provide easy excuses as to why things aren’t working out for them.
Gala, 30
What do you do for a living?
I’m a professional dominatrix.
Does this job get you laid?
It actually works against getting me laid. It’s fucked me up about men.
How so?
Because they’re all freaks. This job has made me realize they’re all liars, hiding something weird about themselves.
Which of the seven deadly sins best defines you?
Sloth. I’m a lazy bitch. Maybe wrath too.
Do you have any sexual regrets?
Yes. I lost my virginity doggie style. That sucked. It’s one of my favorites now, but to lose it that way sucked, you know? I wanted to look at him the first time.
What is your deepest, darkest fantasy?
It’s the same as every girl’s.
Oh?
Getting gangbanged.
Every girl wants to get gangbanged?
If you’re saying you don’t, then you’re a liar.
What’s your most attractive quality?
It would be easier to say something I don’t like about myself, because I like myself a lot. From what people tell me, I’m condescending. I don’t even know what that means — so I don’t know what to do about it. But people tell me that’s what I am, so I guess I don’t like that about myself.
If you could sum up your first time in one word, what would it be?
Awkward.
What’s your favorite sex position?
Reverse cowgirl. I hate that name though.
Got a better one?
Riding his cock backwards?
Diego, 25
What do you do for a living?
I work in art galleries.
Does this job get you laid?
Not yet. Most of the people I work with are older people, like sixty-year-old women with bottle-cap glasses and turtlenecks.
Not your thing?
I mean, I wouldn’t rule it out.
Which of the seven deadly sins best defines you?
I’m more vain than greedy. Can I make up a word?
Go for it.
I’m very “vreedy.” I like money, and I’m a narcissist. I’m an only child so…
If an unattractive woman offered to pay your rent for casual sex, would you accept the offer?
Like fat?
If being fat is unattractive to you, then yes.
A fat ugly girl? Ugh, yeah, I’d do it. But only once a week.
Do you have any sexual regrets?
Yeah, back in college. Two words: “Angry vagina.”
As in The Vagina Monologues?
As in bear trap, as in she was a bitch. Oh, and I got busted by the cops having sex in an alley once. They acted like I was trying to rape her or something.
Why did they act like that?
Because I was having sex in an alley.
When it comes to dating, do you have any dealbreakers?
I don’t really date much. But I guess a white Buddhist would probably do it.
As in a white person who is a Buddhist?
Yeah, because she probably picked it up her sophomore year at NYU. But honestly, my biggest dealbreaker would be a fat person.
Unless she was paying your rent?
Right.
Jessye, 27
What do you do for a living?
I’m a phlebotomist and a nursing student.
Does this job get you laid?
In a sense. I'm pretty sure my boyfriend has some naughty plans for my nursing-school uniform when I am finished with it.
Do you have any sexual regrets?
Just one that I can think of. I had revenge sex with my on-again, off-again guy's best friend. I learned my lesson the hard way about guys who talk a big game. The way he talked I was expecting fireworks. Turned out, he had the smallest dick. Ever.
What’s your deepest, darkest fantasy?
I'm a big fan out outdoor or public sex. It adds an extra thrill when there's a chance you'll be caught. But that's not really much of a secret.
What do you mean?
I’ve had plenty of outdoor sex.
So you’ve already made your deepest, darkest fantasy come true?
Hell yes! A few times. At a state park, a little ways off of a hiking trail, on the ridge of a gorge, at sunset with rain lightly falling. It was like something out of a romance novel. And each time it gets better and better.
What’s your most attractive quality?
I'm told I have a pretty good sense of humor. I'm attracted to people who can make me laugh, and I think a lot of people feel that way. If all else fails, I have pretty big boobs, too.
What’s your favorite sex position?
As boring as it sounds, missionary. It's very intimate and can be as passionate as you want it to be.
Do you have any dating dealbreakers?
A few: chain smokers, guys who are unemployed, guys who live at home, and cats. Cats are assholes. They smell and shed and are selfish. Also, I'm severely allergic to them.
Got it. So no cat men.
No cat men. Dog men, yes. Cat men are probably unemployed and living with their mothers, anyway.
Tristian, 29
What do you do for a living?
I’m a freelance film editor.
Does this job get you laid?
It’s definitely an asset; I work for myself and enjoy what I do. I don’t think it directly gets me laid, but it’s a good card to play. It speaks to other sorts of attributes that women find attractive.
Which of the seven deadly sins best defines you?
I’d say lust or pride. Anybody who knows me knows that I talk about sex all the time. And I’m a pretty vain person. I’m really aware of my faults. Which is good. I feel like a lot of people don’t know how they come across to others.
If you had a word for your first time, what would it be?
Caring. She knew it was my first time, and she just really helped me feel comfortable.
Do you have any dating dealbreakers?
If you don’t believe in evolution. If religion plays a large part in your life. It’s fine if you’re Jewish and not practicing or whatever. But if it’s a part of who you are, then it’s a dealbreaker. Also, if you don’t drink, and if you don’t listen to music. I went out with this girl who was a filmmaker, and she never listened to music. I was mystified, because she works with it all time.
Do you have any sexual regrets?
I slept with this girl. It was a total one-night-stand sort of thing. And then I went to my friend’s house a day later, and she was there. They just ended up hanging out in the same crowd. It was just weird how I had no idea.
Why is that a regret?
Because she was really busted. I mean, like so nasty. Hold on though, I might have a better story. Let me check my phone.
Your phone?
Yeah, I have a list.
You have a list of the girls you’ve slept with?
Yeah, I’m just checking it to make sure that I don’t have any more regrets.
Interviews and photography by Sarah Schwab.
