Sex Advice from . . . Dumpster Divers

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Dan, 34

What dumpster-diving equipment can I incorporate into sex?
You could do something cool with those little grabbers people use to get things off high shelves. A lot of dumpster divers use them. And certainly a good set of heavy gloves can come in handy in a lot of circumstances.

I had sex with a friend of mine after a bad breakup. How can I let him know this was a one-time rebound thing?
There’s got to be a ninety-nine-cent Shoebox card from Hallmark for this. Try to schedule more time with him, but doing other stuff. Say, “How’d you like to go hiking? How’d you like to go to the top of the Empire State Building?” Someplace where there’s obviously not the opportunity for sex.


If I get back together with my boyfriend, should I tell him about hooking up with someone else during our off-time?
It depends on what kind of relationship you had before you broke up. If you didn’t have a relationship where you tell each other all that stuff, then no.

What sexual turn of phrase should be banished from the bedroom?
There are so many. The phrase “have sex” — you’re born with a sex, you already have it, you have it your whole life. The phrase “make love” — love is an intransitive verb, it’s something you do, not something you make. When it comes to sexual terms that actually describe what you’re doing, the only term that’s accurate is “fuck.”

How long should I wait before sleeping with someone new after a bad breakup?
Only as long is it takes to find someone new to sleep with.
How soon is too soon to hop into a new serious relationship?
That’s going to vary by person and by how bad that breakup was, but probably a few months.

Is a partially spoiled relationship worth saving?
As long as part of it’s still good, you can cut out the part that’s gone rotten.

What’s the number-one mistake online daters make?
The biggest mistake is thinking it’s not the real world. The fact that you met someone online doesn’t make them different from anyone else. People always ask, “Wow, what’s it like to have an internet relationship?” It’s like, “I don’t know. What’s it like to have a bar relationship?” You don’t keep going back to the same place after you meet someone, so don’t think meeting someone online makes a difference.

Amylin, 20

AmylinHave you ever found anything sexy in the garbage?
I really haven’t.

What’s the least sexy thing you’ve ever found?
One of my friends found a human finger once.

Get out of here! Where was it?
New Jersey.

What skills do dumpster divers have that can be applied in the bedroom?
We clean up really nicely.

While digging through a lover’s past, I discovered he once dated someone I hate. Now I’m dying to ask him about his relationship with her. How can I get him to talk about it without revealing my snooping?
I usually admit that I snooped. I come right out and say, “I read your email.”

My penis is small. How can I make the most of it?
You should date a tiny girl or boy. Small penises are great for small girls. Being a tiny girl and being not too fond of the penis in general, I find that small penises are better. They’re less intimidating and they don’t hurt as much.

If my boyfriend and I break up temporarily and I hook up with someone else during the time we’re apart, should I tell him about it after we’re back together?
Yes, but leave out details and underrate it. Even if it was really great, be like, “I didn’t come.”

What are some clues that someone is lying in their online personal ad?
It’s often not that they’re lying — they just see themselves differently than other people see them. Usually when people post pictures of themselves, they’re not going to post realistic pictures. They’re going to post pictures that are the most flattering.

What sexual turn-of-phrase should be banished from the bedroom?
Anything that makes you sound motherly or fatherly, like, “That’s a really fine behind.”

My boyfriend and I will be attending an event that my recent ex has also been invited to. How should I handle that? Should I say my hellos alone or introduce my new boyfriend?
That happened to me recently. Actually, they were both exes, one more recent than the other, and the newer ex would have been jealous at the idea of meeting the older ex [had he known who she was]. After he found out, he was like, “I’ve been chatting with your ex-girlfriend for two hours now?” And I was like, “Yeah, you two really get along well.” So don’t make a big deal about it. Treat the ex like a friend. It really isn’t a big deal when you think about it.

Ran, 38 Ran

When is a partially spoiled relationship worth saving?
Relationships don’t spoil in the same way food spoils. When food spoils, it only goes one way. Relationships can recover from being spoiled. To determine if it’s worth saving, you have to figure out if the spoilage can be reversed. Another thing to remember: sometimes it might seem to be spoiling when it’s really just changing into a different form. Certain foods actually get better when they spoil, the way fizzy apple juice is actually better than fresh.

My girlfriend and I hooked up with a friend of hers. It was fun, but now I feel weird around the friend. How can I excuse myself from socializing with her?
I think you should actually challenge yourself and try to hang out with her socially. It’s not good to avoid hanging out with somebody because you feel weird about something physical you’ve done with them. Instead of trying to find a way to not hang out with her, find a way to make yourself okay with it.

What’s the number-one mistake online daters make?
Building a picture of the person in your head based on too little information. Online, you get a very small thread of information about a person, and it’s easy to fill in the blanks with what you idealize. Then you meet the other person and you’re disappointed.

My boyfriend hates going down on me. Should no oral sex be a deal breaker?
It depends on how important it is for you. You have to compare how valuable he is to you versus how important oral sex is to you.

How long should I wait after a breakup before sleeping with someone?
It really depends on how the breakup went. If someone dumped you, it’s important to go through the grief, instead of trying to immediately find somebody else to fill that space. It’s paradoxical — the worse you feel about it, the longer you should wait.

Where can I pick up a dumpster diver?
Spending all day at the dumpster is not a good idea. But there’s overlap with dumpster divers and other groups: anarchists, Critical Mass bicycle rides, Food Not Bombs and punk shows. So at any of those groups’ events, there’s a good chance of meeting a dumpster diver.

What’s the sexiest thing you’ve found in the garbage?
I found a case of olive oil once. That’s a little bit sexy.

Rob, 36

Have you ever found anything sexy in the garbage?
Well, yeah. Porn. I’ve found magazines, a stray VHS. I found some really weird stuff once. I’ve since gotten rid of it. It was a comic book about bestiality called Mom Goes to the Dogs. Shred your documents, that’s all I can say.

When does “I just need some time” really mean “Our breakup is imminent?”
You have to look at other factors. Analyze the situation as a whole. “I just need some time” sounds like people in their early twenties, and that’s fine. I’m going to tell you the secret to a lasting relationship: hardship. The reason there’s so much — oh, let’s call it turnover — in intimate relationships is that we’re all sitting pretty. The relationship will be saved by external hardship. When it’s just as easy to go your own way as it is to be with a person, you’re probably just going to go your own way.

If my boyfriend and I break up temporarily and I hook up with someone else while we’re apart, should I tell my boyfriend about it after we’re back together?
A guy would probably find it interesting or exciting. I mean, life is pretty boring. That sort of soap opera is pretty rare in my life. So yeah, if you want to keep it interesting, tell him all about it. I remember I had a girlfriend when I was in my early twenties who told me all about her sexual history. It infuriated and excited me at the same time.

When is a partially spoiled relationship worth saving?
Well, I was a real jerk to my wife the first couple of years. I was not used to monogamy. So I guess I partially spoiled the relationship by being a complete asshole. And she didn’t divorce me. So I now have the answer: When there’s still a long-term chance that it will work, when the fundamentals are good, then it’s worth saving despite the screw-ups.

What’s the best way to initiate makeup sex after a fight?
When I was in the Army, I had a girlfriend. I was in my twenties, and I was very stupid. She was telling me this sensitive story about how she went to visit her father’s workplace. He was a railroad man. She found the business card of a prostitute among his things, and she realized that her father was cheating on her mother with prostitutes. In a television drama, this would be a music-playing moment.

All I could think to say was, “Were there kissy lips on the prostitute’s business card?” I mean, a prostitute has a business card? What did it look like? What font was her name written in? And she took off running — we were both on the running team in the Army. I ran after her, and I caught up to her. And when I caught her, I grabbed her by the shoulders, pushed her against the wall and kissed her. It worked. Works every time.

Is cheating ever okay? When?
When you’re not parenting minor children, it’s okay. It’s all about the interest of the children. I have a personal affection for my wife. I would stick with her even if we didn’t have a young child. But I am fanatically against destabilizing a household where there’s children. When there are no more children, you can take your life back. But there’s a sentence of eighteen years when you decide to have a kid.

What’s the best way to win someone back after a break up?
You just have to be persistent. The greatest lady-killer I ever knew was a very unattractive guy who was a complete sociopath and had no conscience whatsoever. I watched him fake crying to his girlfriend and I couldn’t believe she didn’t see it. So the less conscience and the less honesty, the better. That’s what works. I had a conscience and that didn’t work. I had to learn a foreign language just to get laid.

Was your whole foreign-language class single dudes?
Oh yeah. And they weren’t Don Juan types either. You find a guy who knows a second language — not one he knew from childhood, but one he learned as a student — and he did it because American girls weren’t putting out. Or at least not the ones he was interested in.    

Interviews by Kate Sullivan. Sex Advice From… appears on Thursdays. Have questions for the general public? Send them to

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