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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 sitefor 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.

Comments ( 20 )

What's next, sex advice from Oscar the Grouch? Harry's a wise old brother, but I wouldn't recommend a nice white jacket like that on the stoop.

bearman33 commented on Oct 08 10 at 12:14 am

Harry respects women only because he doesn't want their potential husband to "beat his brains out' ? So not wise...

Monica commented on Oct 08 10 at 12:53 am

great advice from three awesome dudes

jac commented on Oct 08 10 at 3:30 am

"make babies at home" - sage advice, indeed!

mudpie commented on Oct 08 10 at 9:43 am

Harry is hilarious! I was surprised he didn't tell kids not to have sex. He told them to just go back home to do it.

LoveHandle commented on Oct 08 10 at 10:45 am

Monica - Harry didn't say he respects women "only" because he doesn't want to potentially catch a beating. In fact, he doesn't even use the word "only." If you really read what he's saying, it comes off like he truly does respect women. He may want to signal his approval of a woman through a whistle or words, but he gallantly restrains himself. So that is wise advice for young men.

bearman33 commented on Oct 08 10 at 11:25 am

According to these guys, there's a lot of sex going on in the park. How can I get in on these pinecone-fueled sex orgies?

Tonjiboy commented on Oct 08 10 at 11:42 am

"Only have sex where you pay the rent." Wise advice. And I read all of Harry's comments in my Harry voice!

poyote commented on Oct 08 10 at 6:13 pm

these are fantastic. hooray older people! they give the classiest advice

sylvia commented on Oct 08 10 at 10:42 pm

i agree with sylvia. these people all had stuff to say thats actual good advice. i like the first guy a lot.

andrea commented on Oct 08 10 at 11:34 pm

Poyote, I wanna hear your Harry voice! Can you describe it?

Demanda commented on Oct 09 10 at 12:25 am

this is hilarious!

ss commented on Oct 09 10 at 12:14 pm

You need to get off that stoop and get inside the house with my mother:)

brittney commented on Oct 09 10 at 12:29 pm

@Monica - I'm with bearman, and I'd just like to add that it's more a further justification. Much like what he says later about his friend marrying his ex and then getting divorced: "That goes to show you it's not right."

superchicken commented on Oct 11 10 at 12:33 pm

The first Michael had some of the best advice I've seen. When you have to talk about an issue with someone you're dating, don't tell them there's a problem and sit them down at a table or something. Talk things out in the moment. I wish I knew this like four years ago.

Kate commented on Oct 11 10 at 12:52 pm

See Harry is an original..."play Al Green, Marvin Gaye, Sam Cooke..." Word!!!!

CJ commented on Oct 11 10 at 5:19 pm

Back alleys in the Financial District? That Michael's one classy gentleman.

bearman33 commented on Oct 11 10 at 8:20 pm

How about "Sex on stoops with men giving advice"

HailRobonia commented on Oct 12 10 at 9:06 am

How about Bob Stoops giving football advice while his wife blows him?

bearman33 commented on Oct 12 10 at 1:13 pm

Holy god! Advice from people who aren't twentysomething self-obsessed hipsters? Hooksexup, you are Doing Something Right! Keep it up.

Joe commented on Oct 12 10 at 1:13 pm

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