Advice

Sex Advice from Men Sitting on Stoops

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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.

MichaelMichael, 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.

HarryHarry, 71

What lessons have you learned about love from your days on the stoop?
I used to sit on the stoop and watch everyone walk by. That’s how I met my ex-wife. I saw her sometimes, and we wanted to be together, but her parents kept her inside the apartment – she was an only child, and they were very strict. I’d see her cousin, and say, “Tell your cousin to come downstairs so I can see her.” Then her cousin would come back and say, “She told me to tell you to go to hell.” I got her downstairs finally. My cousin had a room two buildings down, and he said I could use it. Believe me, I did. That’s how she got pregnant. I was nineteen; she was seventeen.

How much PDA is too much PDA?
That, I wouldn’t do. It’s not nice. Don’t go out in the park or on the streets kissing. There’s kids out there in public. Do it in the house where you live at.

If I'm hanging out on the stoop and I see a beautiful woman walk by, what's the best way to let her know? Do catcalls ever work?
Give respect. Always give respect to a lady. I see guys all the time getting fresh with a lady. How do you know that lady’s not married or something like that? Give a lady respect. She’s coming home from work or something. She’s got a family. I don’t want some woman coming around the corner, bringing her husband to beat my brains out. Heck no!

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?
Here’s what you do: go to a party or a dance. Or you can go to a bar – wait, no, don’t go to no bar. Both of you have fun. If you drink, don’t drink too much. If you both get that feeling dancing and going on and you really care for each other, come on home and get in bed. And then play Al Green, Marvin Gaye, Sam Cooke, and all them.

My new boyfriend is friends with his ex, and it's starting to bother me. What can I do to keep an eye on him without seeming too possessive and jealous?
I think people should go their separate ways after they end their relationship. Keep in touch and see how they’re doing if they’re sick or something happens in their family. You can ask how they’re doing in their new life and all that mess, but move on.

A girl who casually dated one of my friends recently asked me out. Would it ruin my friendship if I said yes?
If I were your friend, I wouldn’t want to be in your company if you dated someone I used to be with. If something happened like that to me, I’d rather just find a new person who doesn’t know my friend. My friend and I used to drink together every day. When I divorced my ex-wife, she married him. They had one son together and then they separated. That goes to show you it’s not right.

So, “bros before hos”?
I’m not too familiar with that saying. But I wouldn’t fall in love with my friend’s girlfriend.

I really want to try sex in public, but I'd really rather not get caught. Any tips for a good first-time spot?
Oh, man. I have to take two Anacin when I go back in the house. Only have sex where you pay the rent. You don’t do it in public. I go to Central Park everyday where young kids are hugging up when they’re supposed to be in school. It’s a disgrace. If they’re skipping school, and their parents are going to work, they should go back to the apartment when the parents leave. Make babies at home.

MichaelMichael, 42

What lessons have you learned about love from your days on the stoop?
Number one: never look at another man’s woman too long, because you wouldn’t want that done to you. Number two: if you think you’re going to say something wrong, don’t say it at all. A simple “hi” and “bye” is quite sufficient.

What's the best way to check out someone I see on the street, without looking creepy?
Well, that’s why I wear this low hat. Nah, but you don’t need to look too long. Take three seconds to get an eyeful – my lady gave me that limit, and I give her the same limit.

I'm kind of attracted to a girl I always see hanging out on a stoop in my neighborhood. How should I approach her?
Just stop and say hi, or make a casual comment. She may be shy and thinking that you don’t want to talk, or she might not pick up the signs. If she’s not attracted to you, she won’t think anything of it. If she is, she’ll be glad you stopped.

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?
More than likely, he’s having an affair, or you’re having second thoughts. You’ve got to remember what brought you to the person. If it dies down, you’ve got to spark it up. One of you has to be the firestarter. You can start by being naked when he comes home one day. That always works. A guy can bring his woman flowers like he used to, because he probably doesn’t anymore. Go out on small dates. Do what you did when you first met — whatever you did to get each other has to be brought back.

I hate having sex with quiet people. What's a nice way to tell them to make some noise?
If the sex is good, quiet is okay. Either she’s a screamer, or she’s not. You can turn up the music, but other than that, you have to get ‘em drunk.

My girlfriend and I want to have a threesome, but we've never done it before. How do we prepare? How should we choose a third person to join us?
The ultimate question is if you’re going to choose a man or a woman. I think for a man, it would probably have to be another woman. I’m not gay, so a threesome with another woman would be quite all right. I’m not homophobic, but men would rather have sex with two women. It would have to be a person you don’t know, and who your partner is attracted to. But hopefully, you don’t have to revert to a threesome. There are ways to spice up a relationship before planning a threesome.

I found a picture of my brother's girlfriend on a dating site for lesbians. Should I tell him?
Oh, yeah. Tell him his girlfriend is bisexual. I’m pretty sure he must know about that anyway. I don’t see the harm in that, but I’d definitely tell him.