Love & Sex

Talking To Strangers: Chicago, IL

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Nerve asks deeply personal questions to people we just met.

Angie, 22

Do you have any crazy exes?
Most of them. When I first moved back to Chicago I met this really attractive Englishman who was sort of homeless. He moved into my house, we had amazing sex for seven months, then he sold all my things for crack money and transgendered prostitutes.

He wasn't, like, homeless homeless — he had a buskers license, so he was a professional public performer. But then his license ran out, and he didn't bother getting another one, and suddenly needed money for crack. And transgendered prostitutes.

You are making this up.
No! I'm not! I mean, I kind of knew about the crack habit, but it didn't really bother me because what you do to your body is your business, so long as you're not hurting anyone else. But then, well, you know. He sold all my shit in one big go, and then tried to take my cat. I mean, really? You're going to be homeless, on crack, and I'm supposed to let you take my cat, too?

Is the sex better or worse with homeless guys?
They're definitely more grateful, if for nothing else than to be indoors. It is a lot harder to tell them to go home, though.

Do you have any dealbreakers?
Well, if you can't tell yet, I'm pretty open-minded. Although recently I was with this one guy and he just decided to go on ahead and try eating out my asshole.

With or without a warning?
No warning, just forging ahead. I let him roll with it, because, hey. People do it. I was not a fan. That move aside, however, he was the single best lay of my life. Amazing. He's a delivery biker here in the Loop. I highly recommend keeping an eye out for him.


Ramon, 27

What do you do for a living?
I'm a property manager.

Do you meet a lot of people that way?
No, there's a bit of a conflict of interest there — plus I just wouldn't feel comfortable meeting people that way. I go out, meet people through friends or at bars. You know. Normal stuff.

Have you ever been offended in the bedroom?
Offended? No. I've had awkward situations, though.

Such as?
Well, there was this other girl who, I don't know, just would not leave me alone. So we go on a couple of dates, and it's alright. It's nothing spectacular — she's from South Carolina, and she's really forward, and she's really into metal, and I'm… not any of those things. But eventually, she calls me up and asks me to come on over to her place, which is always a good sign. So I get there, and she answers the door in this tiny white nightie thing, and there, behind her, is a giant Confederate flag posted up on the wall.

Yes. And so, in my head, I'm torn between this girl splayed out on the bed and this desire-killing flag that I can't get out of my mind. So I'm like, "Uh… how about watching a movie?" As the night progresses she just keeps acting stranger and stranger, sort of pushing me to be more aggressive and flopping over the bed and eventually I realize that I've stumbled into someone else's rape fantasy. Finally I just — I'm like, "I can't do this." I just couldn't. 


Molly, 28

What do you do for a living?
I've been working at GMart Comics for almost two years.

Have you ever gotten involved with anyone through the comic shop?

That was quite a long pause.
I guess that's a yes. Very much yes. But, there were some… complications. I do have a lot of people hit on me. A lot of the awkward leaning-in, trying-to-be-smooth stuff, asking "What have you been reading lately?" And I'm really friendly, so I'll talk with them. The vast majority of our customers are guys, so it happens a lot, but we're getting a lot more women coming in. I was recently hit on by a girl, and even though I wasn't interested, that was kind of awesome.

Do you have a type?
Yes! Apparently — and I don't try for this — I have, for the last, like, ten years, wound up dating Roman Catholic, Sagittarius guys with facial hair and some sort of musical talent.

That is extremely specific.
I know! And I'm not even Christian, which usually becomes a problem.

How much does sex factor into these relationships?
A lot. I mean, I obviously don't subscribe to the same philosophies, but if you care about someone you're going to be respectful of the things that matter to them. One of my first serious boyfriends was very insistent that he was not going to have sex until he was married. We did fool around a lot, though. But no sex.

Are you seeing anyone now?
Yes, and he, too, is very religious — he's studying to be a pastor. So that can make things a little tense sometimes. We've been together for around a year, and it's been a little difficult for me, because it means that I haven't had sex for a year. And I had a very active sex life before we got together, and I mean, we still fool around with each other, there are still sexual things going on, but we have not had actual, physical, textbook sex.

You seem pretty okay with that.
Yes! I am. It relates to how I feel about him and my past experiences and… I don't want to say "mistakes," but places that I don't want to go again. So I'm definitely okay with it.

Lauren, 26

What do you do for a living?
I'm an artist — I paint and animate.

Do you get a lot of dates that way?
Yeah, I'd say so. I think guys like the fact that I'm creative.

Do you usually go for artists yourself?
My first few boyfriends were musicians, and I eventually moved onto artists. But then, I used to be a musician and turned into an artist, so I guess I was looking for people with interests like mine. Although, now I guess I'm dating a musician again — a sound engineer. So it varies.

Has the stereotype of "sensitive artist" shown to be true in your relationships?
Yeah, I think it has. I mean, I've dated aggressive guys before, and that was really fun, it's nice to have someone who knows what they want and who takes control over you. But a lot of the artist types need a little prompting and encouragement to get going. It's like they're afraid. They can be a little too passive, and that can get very boring.

Do you have any expectations when you get in bed with someone?
I don't think so. No. One of my philosophies is to have low expectations so that I can be happy with whatever I get. I mean, if the sex isn't great, I probably won't stick around. Or maybe "great" isn't the right word — if it's not, you know. Doing it for me. But yeah, I don't go in assuming anything — low expectations mean you'll never be disappointed.


Alen, 24

Do you have a type?
Uh, at this point? Ethnic girls.

Do you have any crazy exes?
Actually, I think I'm the crazy ex. I used to think about this when I was reading Scott Pilgrim, like, "Wow, I wish I had a league of crazy ex-girlfriends." It seems like such an efficient way to vet future relationships. You know, you get into relationships and then you get out of relationships, and it's pretty quagmire-ish and I don't handle it well.

Do you have any fantasies?
Well, I was reading Savage Love for a while and it came up that every girl's fantasy now is to have two boys — sort of a Bella Swan complex. And once that concept was presented I thought, "Oh, man, I'd be totally into that." But again, as with the Scott Pilgrim thing, that's me putting myself through another gender-swap here.

Maybe that's the fantasy.
If gender-swapping is my fantasy, I'm going to need a lot more than an interview with to sort my shit out.

Who's the boss in your relationships?
I think the person in charge of the relationship is whoever likes the other person less.

It's usually true, though. I don't really have a positive outlook when it comes to these things.

Would anything make your outlook more positive?
I don't know. Robots, I guess. A robot girlfriend.

An ethnic robot girlfriend.
Now we're getting somewhere.  


Nikita, 26

What do you do for a living?
I work for a company in the West Loop doing sales.

Do you get to meet a lot of people that way?
People I'd want to date? No. But I did get to go to this electronics show in Vegas — it's the only time they've ever let me out of my cubicle cage. I'm kind of their sales bitch. Anyway, I had some spare time, and I wound up sneaking into the Adult Video News porn party next door.

You have to tell me what goes on at a porn party.
It's insane. It was in the Hardwood Suites, which is this massive suite in the Palms where they have basically everything — there were basketball courts actually in the suite, and they'd put stripper poles into the courts. There was also this pool table with a midget on top performing with a dildo.

As in this midget stripper is standing on top of the pool table with the dildo going in and out. And I'm there with my jaw dropped, trying to take all this in, and the porn people are just standing there, enjoying their drinks, not even really noticing anything that's going on.

Did they notice that you didn't belong?
Well, I was definitely overdressed. I mean, I was appropriately slutty but not porn slutty. But I snuck in with some people from GQ, who were also not invited but, you know, they were from GQ so no one cared.

Do you think that porn has affected peoples' sex lives?
Oh, definitely. Just the other day I was talking with a friend about how she doesn't like to swallow her boyfriend's come, and he'd asked her, "What are you talking about? Everyone loves it!" But they don't. The only reason everyone thinks girls love it is that, in porn movies, girls not only act like they like it, they're spitting it into other girls' mouths, like, back and forth, back and forth, and it's like, really? No. I'm so happy to be in a committed relationship so that I don't have to go out and deal with that sort of craziness.

Except when you sneak into porn parties.
Well, come on. You're at a work convention and the party next door is filled with naked porn stars and a self-pleasuring midget. You wouldn't?

Interviews and photography by Jaime Calder.