Sex Advice From Men Sitting on Stoops

Q: What’s the best way to pick up someone sitting on a stoop? A: Take three seconds to get an eyeful, and keep moving.

By Amanda Green

Michael, 52

What lessons have you learned about love from your days on the stoop?
This isn’t even a proper stoop. I used to live in the West Village in a building with a real stoop. But I’ve always liked to sit on the stoop and watch people. You get to know the neighborhood. I’d meet people, and I’ve dated men I met when I was sitting on a stoop.

How’d that happen? Did you see men walk by and holler at them?
If I were on a stoop facing the street, I could look down the street to see if there was someone interesting coming and then, you know, cruise him. I might say hello, or just make eye contact and, when he walked by, see if he looked back. Then there’s this weird dance that happens. “Do I talk to him, does he talk to me? Do I follow him?”

Sometimes people just stop and say hey and sit down. Then the conversation becomes “Do you live here?” In terms of picking people up, it’s very convenient. I don’t do that anymore, though.

What's the best way to check out someone I see on the street, without looking creepy?
Do what I did! Be subtle. Be nice. A smile goes a really long way.

I'm attracted to a girl I always see hanging out on a stoop in my neighborhood. How should I approach her?
Just say hello and something like, “I see you in the neighborhood all the time. Do you live here?” Ask questions and listen. Talk less. Be present. Listen for that thing you have in common that you can discuss. This girl might be a really cool person, and she might never live up to your romantic expectations, but take a moment to see.

My boyfriend and I have a great relationship, but lately, we've been having less sex. What do you think might be going on? How can I kick our sex life back into gear?
That happens naturally — sex comes and goes. Spend more time together, because people get really wrapped up in their separate lives. Make a date night, and go back to that place of asking questions and listening. It’s far better than sitting someone down and saying, “How come we haven’t been having as much sex? Something’s wrong.”

I hate having sex with quiet people. What's a nice way to tell him to make some noise?
With anything like that — if you want to talk about turn-ons or something your partner isn’t doing — it’s got to be in the right moment. Tell them what you like and listen to what they say. But ask at the right moment, so they don’t get defensive. Either that, or make them make noise. You don’t make noise? I’ll make you make noise!

My ex dumped me because he thought our relationship was getting too serious too quickly, but now he can't stop emailing, calling, and texting me about what a mistake it was. Should I give him another chance?
Yes, but be cautious. As a friend of mine said, “The first time you fuck me over, fuck you. The second time you fuck me over, fuck me. The third time, there is no fucking.” The first time someone makes a “mistake,” it’s okay, but fuck you. The second time it’s “fuck me,” because I let you do it. If you knew someone did it before, you’re taking a risk letting him back in. And there is no third time.

I really want to try sex in public, but I'd really rather not get caught. Any tips for a good first-time spot?
Central Park has tons of places at night, but don’t go too far in. Maybe if you had a big dog, you could take it with you and tie it somewhere. If the dog starts barking, you’ll know someone’s coming. Maybe back alleys in the Financial District, because it’s abandoned at night. Empty lots. A balcony or a fire escape would be hot.

I found a picture of my brother's girlfriend on a dating site – for lesbians. Should I tell him?
No. I don’t believe friends should tell someone else about their partner. You don’t know their arrangement. He might understand that she’s bisexual, and they’ve worked something out. It’s no one else’s business to get involved. If he gets hurts, he gets hurt. But I think it could cause more trouble to get involved than to just keep quiet.