Love & Sex

Talking to Strangers: Chicago Pride Parade Edition

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Nerve asks deeply personal questions to people we just met.

Michelle, 32

What do you do?
I'm a project manager for a print company.

What's your sexual orientation?

What's your relationship status?
Dating. It's going well; it's my first relationship.

What attracted you to him?
A good body. I'm just going to be honest. And creativity! I wanted somebody in the creative field.

How do you impress guys?
You've got to play it cool. Got to fuckin' play it cool. Women are crazy; you can't act crazy. Just act fuckin' normal.

Any embarrassing or funny hookup stories?
Well, my embarrassing one: I was hooking up with somebody, and he threw up, and he tried to eat me out afterwards, and I was like, "Get the fuck out of there!" And that was the end of that. That was a friends-with-benefits relationship. Oh, I've hooked up with a couple of C-list TV stars. That's always worth it. They always try really hard, because they know you're going to tell your friends and they know you're going to blog about it.

Can I get any names?
Nah, I can't give you any names. They're in commercials and bad TV shows.

Are they as good-looking in real life as they are on TV?
No, they put on a lot of makeup. Maybe I should have made them put on more makeup before I went to bed with them.

But they don't disappoint?
No! That's why I hook up with them. I wouldn't hook up with anyone ugly.

Where do you meet these C-list celebrities?
Just around town! The older you get, the more time you put under your belt. When I was twenty-two, I was like, "I never meet anyone famous!" and now I'm thirty-two and I'm like, "Oh, I know that person." You just have to put your time in.

What's the most unusual place you've had sex with a C-list celebrity?
In a hammock. And I do not suggest it. It's the worst! You can't get good leverage and there are ropes everywhere. Hammocks are bad.

What's the craziest thing you've done to get laid?
Wearing a lot of balloons at the pride parade? No… just drinking. Drinking all the time. Oh, I broke into somebody's house. I told him I lost my keys and needed somewhere to sleep, so I broke into his house.

Did that work?
It didn't work. We snuggled in his bed.

Well, at least he welcomed you in after all that.
Yeah, he let me in. Actually, his landlady let me in. That's the most embarrassing part.

Gay marriage was just made legal in New York. Do you think it'll happen here?
Thank God! And yeah, I give it a year. Five years, max.

Rahm Emanuel, the Mayor of Chicago, is the grand marshal of this parade. Would you have sex with him?
Only with that weird finger that he's got. That weird missing-finger nub? Yeah, I would let that happen. He kind of looks like Skeletor.


Tom, 41

What's your sexual orientation?
I'm gay.

What do you look for in a guy?
A guy who is all about commitment, mutual understanding, and going along for a fun ride in life.

How do you impress someone like that?
I'm a hopeless romantic, so I'm all about just getting to know somebody — getting to know where they came from, who they are, what they do, and whether we have mutual interests. Then if we click, we click!

That's almost old-fashioned these days.
I don't know if it's necessarily old-fashioned. Some people tend to think it is, but I think there are more people out there who want it than don't. We tend to forget the simple things in life. Family, friends, love, mutual respect, and understanding. And just plain fun.

Sounds good to me! Any embarrassing hookup stories?
There was one time when a couple friends of mine took a dare to see who would be a better kisser: a gay guy or a straight guy. I won.

Nice! How many people did you have to kiss?
Five or six.

What are the rules of a kissing contest? You kiss the judges, and then they decide the winner?
Yeah, that was about right. It's totally harmless, totally fun. That's what life has to be about. You need a good laugh.

What's the most unusual place you've had sex?
In an elevator on the way up to the CN Tower. Unfortunate, the elevator malfunctioned a little — it stopped in-between floors. Oops! We got in a little trouble, but it was well worth it.

What's the most desperate thing you've done to get laid?
You know, I'm pretty vanilla. I don't know if I believe in crazy or desperate. It's just natural attraction. If it clicks, it's right there in front of you.

Do you believe in love at first sight?
Yes. It may be the hopeless romantic in me, but I think you can look at a person and see their smile and see how genuine they are inside.

Do you believe in soulmates then?
Yeah, I do. I believed at one point that I had a soulmate and that didn't work out, but sometimes that's what life does to you. Sometimes life just kind of takes you in a direction where you find that one person.

Gay marriage was just legalized in New York. Do you think it'll happen in Illinois?
I think it will. I was actually married in Toronto with a long-term partner who I was with for ten years. It was the first year same-sex marriage was legalized in Canada. Unfortunately, that didn't work out. With that, I was able to learn more about protections and freedom and respect for all people, and I really do believe that people need to wake up and realize that the freedoms in this country should be for everybody.

What did you learn from your first marriage?
I learned that sometimes people don't understand what commitment is, but I think you can find that in both a straight and a gay marriage. But I do believe that there are a lot of people who are in for the long haul, because I certainly was.


Angela, 28

What do you do?
I work at a hospital in Joliet.

What's your sexual orientation?
I'm bisexual.

So what's your relationship status now?
I'm married to a man. He's straight. I was actually dating someone at the time and I cheated on him with my current husband.

How does your current husband feel about the fact that you cheated on someone with him?
He said, "Either you take him or you take me." But honestly, I was so sick of the bullshit that was going on with my ex after three years that I decided to say "fuck it" and take a chance.

What does it take to be in a committed marriage?
Holy fuck, I don't even know how to answer that. I was in love. I was crazy. I want it all. I want bitches; I want men. I think our next step is a threesome with another chick.

Have you ever been in a threesome before?
Absolutely not, but I'm willing to do one right now with you.

I'm flattered — do you think your husband would be up for that?
Uh, absolutely.

How long have you been married?
Five years.

Yeah, sure.

What's the difference between being with girls and being with guys?
Well, I'm attracted to both, so it really doesn't matter. I love males, but I think women are sexy as hell and I will basically do whatever it takes to get with either-or. Besides the obvious reasons, I think women are more intimate and men just want to like, get you in the ass and call you "slut" and shit. Women are more intimate. I love grabbin' titties… can I say that?

You can say whatever!
I can say whatever! Fuck it, then! Shit! Hell yeah! I love suckin' titties, I love suckin' pussy, I love suckin' it all.

Any crazy hookup stories?
I had sex in a mall bathroom one time. That was kind of fun. I just kind of grabbed her and uh, stuff happened.

Has anyone ever offended you in bed?
Absolutely not. It's hard to offend me.

Gay marriage was just made legal in New York. Do you think it'll happen here?
Absolutely. I think it should! I think you should be happy no matter what you are or who you are.



Johnny, 25

What do you do for a living?
I'm trying to get into the medical field, whether as a physician's assistant or whatever. I'm taking a couple of courses now.

What is your sexual orientation?
I'm straight.

What's your relationship status?
My girlfriend of three years broke up with me last week. After a funeral.

That's terrible!
It's okay.

How are you taking it?
I'm pretty fine so far. I was convinced to come here because my best friend's girlfriend, who's hot, told me to get dressed up. So I said "Fine, whatever."

Great reasoning. Are you planning on jumping back into the dating pool, or are you going to take a break?
I would like to start dating again. People say that I'm really good on my feet. Not to mention that I've been hit on today like twelve times, by both males and females.

There are a lot of possibilities here.
Eight guys, four women. But I'm going for the women.

What are you looking for?
If I see a woman, I want to see a smile. If I don't see the right smile, I can't deal with it. She has to have eyes that are really attractive. Maybe like hazel brown? And a good laugh.

How are you impressing the ladies who hit on you?
Well, when I was trying to get ladies just to get with them, I had a line.

Lay it on me.
My favorite line is, "I just came back from the future, and I saw that you and I are still together ten years from now."

How many times has that worked for you?

Your luck might change today!
I've used it four times, but still, zero-percent success rate so far.

Any crazy hookup stories?
One time, I ended up streaking for a girl who later ended up being a regular weekend fling. It was a bet I had lost in a beer-pong match. We were drunk. I lost, I streaked.

How long were you guys hooking up?
Two years. We were Ashton Kutcher and Natalie Portman before that movie came out. They based it off of us.

Oh really? What's the most unusual place you've had sex?
I was in a car, parked outside a university. The car was shaking, and a cop stopped by to check in on us. He said, "I'm not going to report this. Just finish and go." Those were his exact words.

Was it hard to finish then?
No, it was like I had the stamp of approval.

You didn't feel any pressure from the law?
No, but I did want him to walk away so I could finish quickly. Then I tried harder to go faster.

What's the craziest thing you've done to get laid?

Do you have a special song?
I pick "Those Summer Nights" by John Travolta and Olivia Newton-John, and instead of singing "Wonder what she's doing now," I sing, "Wonder who she's doing now."

I see what you did there. Does it work?


Grace, 24

What do you do for a living?
I'm a student.

What's your relationship status?

Congrats! When you met your fiancé, how did you impress him?
I was actually dating one of his friends at the time and I guess I just tried to be myself and to be really comfortable around him. I just tried to be curious about what he was doing. He didn't put up a front. He didn't try to be a different kind of person around other people. He was always the same. He was really motivated. He worked really hard and knew what he wanted to do with himself. He wasn't lazy.

How did he propose?
It was on our anniversary, and I knew he had my grandmother's ring, so I was thinking it was going to happen that night. I thought it was going to be at dinner and I was getting nervous about a public proposal and how I was going to deal with that. But he actually just woke me up, with roses all around, and came into bed with me and proposed just as I was waking up. It was perfect.

Do you have any funny or embarrassing hookup stories from your past?
He's right behind me, so hopefully he doesn't hear me, but the one time a friend and I were at a hostel in Barcelona and we brought guys back to our room. There were like, fifteen people in one room. It was probably not the smartest thing, but I was young and stupid.

Any crazy exes?
Oh God, yes. Once, when I broke up with someone, I found out he had had two other girlfriends when he was with me and when I ran into him a year later, he still said he was in love with me and wanted to come back to me. It was laughable.

What's the most unusual place you've had sex?
On a dance floor.

Were you at a club, then?
Yeah, it got pretty intense. Definitely.

Do you believe in soulmates?
I do, but I don't think there's only one. I think you can find a soulmate and if it doesn't work out, there are other ones out there as well.

Gay marriage was just legalized in New York. Do you think it could happen here?
Yes. I think we'll be one of the next states to go. For sure.

Would you have sex with Rahm Emanuel?


Rudy, 67

What do you do?
I'm retired. I live eighty-something miles from here. I've been wanting to come to this parade for over twenty years. I decided today that I was going to come. Took two trains to get here with my son and I'm having a ball.

What's your sexual orientation?
I'm male. I'm one-hundred-percent male. But I have no qualms with whatever a person decides to do. You live and let live.

Does that mean you're straight?
Yes. Like I said, I'm all man. I'd like to get the opportunity to tell you. Since you're working now, maybe we can meet up later. You will know I'm a one-hundred-percent man.

Oh, really! What's your relationship status?
I'm widowed. My wife died from doing drugs.

I'm so sorry. How long ago was that?
Four years ago. I haven't had any sex since then, so I think you're taking a chance on interviewing me at this point.

Are you sexually frustrated?
Not really; I enjoyed myself as a youth. As a youth, I was really wild until I got married. I think I had enough sex by the time I was twenty-five to last me until seventy-five.

Do you have any crazy hookup stories from your past?
Well, once I was a Chicago city bus driver. Me and a couple friends of mine stopped in at a place on Halsted, and there were these five ladies sitting at the bar. We walked in, we partied, and I grabbed one of the ladies, and when she stood up, she was six-foot-five. I didn't pay any attention to that, but I was a little embarrassed because she was much taller than me. So we danced and when I got back to the table, I told my friends, "Wow, I feel like I was just dancing with a man!" and they said, "You were."

What normally attracts you to a lady?
Just somebody honest and cute and about… twenty-five years younger than me.

How do you impress somebody like that?
With my fingers crossed.

What's the craziest place you've had sex?
I don't know if there is one. But at home, my cat's been trying to get in my bed. She's been licking herself a lot lately, tryin' to get me hot, but I refuse.

Oh, so your cat's trying to turn you on? What's the most desperate thing you've done to get laid?
Nothing. I'm the kind of guy that just prefers love and affection. I have never paid for sex in my life and if I never have sex again, I'm okay with that.

I'm sure some ladies like to hear that.
I'm an affectionate kind of guy.

Gay marriage was just legalized in New York. Do you think it'll happen in Illinois or Michigan?
It might. I'll tell you this: I'm from the old school. I would've never thought that things that are happening now would come about. The new generation has a lot of dealin' to do with life. Quite a few more things to deal with than I had to deal with.

You said you've been wanting to come to this parade for twenty years, why this year?
Because I was able to save enough money for the two trains.

Was it worth the trip?
Oh yes, really. Especially you.

Interviews and photography by Ruth Tam. Want to talk to strangers in your town? Email