Sex Advice from . . . Private Investigators

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Anthony, 47

What are some clues that my significant other is cheating?
Check their cellphone bill. Look at the call times. They call their lover on their way to work, during their lunch break and after they meet with them to make sure they got home all right.

Can a relationship survive after someone's cheated?
Yes. If a woman's husband is having an affair with Debbie, Debbie is not the problem. There's a problem in the relationship. If the husband breaks it off with Debbie and they don't solve the problem, then there's going to be a Sally, and then a Victoria.


My boyfriend of two months was a virgin when we met. He says he wants to be monogamous, but I'm afraid that if he doesn't sow his wild oats now, he'll cheat on me later. I'm thinking about letting him sleep around for a bit just so he can get it out of his system. Is this ridiculous?
An open relationship is the worst thing you can do in this situation. Once he knows he can see other women, just the idea of sleeping around might turn him on more than a loving relationship with you does. Ninety percent of all people who get married under the age of twenty-one get a divorce. People get the seven-year itch because their goals in life become different.

How long should someone wait after a bad breakup before having sex?
Three to six months. With the holidays coming up, people will be jumping into bed with anyone because they're lonely, and then when January comes around they're alone again.

I had a threesome with my boyfriend and my best friend. Afterward, all three of us agreed it was like having the best of all worlds. Could this be the beginning of a successful three-way relationship?
It's never going to work out for the woman. We actually know people who were like that when they were dating, a woman and a man with other women. Then the man decided he wanted to be exclusive. That's a no-win situation.

I just found my girlfriend's "relationship book." In it, there are written plans for a hypothetical wedding: what our song will be, prospective seating charts, the whole bit. We've only been dating a few months. Should I be freaked out?
I think that's a great thing to find. Here's someone who loves you. It doesn't mean the wedding has to happen next month. You should just be glad she feels this way about you. If you want to bring up the topic to know where she stands, say something about marriage, hypothetically, and see how she reacts.

What's the best way to get a private investigator to go home with you?
It's like hunting season with a duck pond in your backyard. We had a woman come in one time, back when I was single; she was drop dead gorgeous. She said, "I think my husband is having an affair," and I asked "Why is that?" She said "Because I haven't had sex in six months." And I said, "Ma'am you have come to the right place."

Danine, 38

What are some clues that my significant other is cheating?
Changes in behavior: a sudden interest in working out, a new work schedule, hanging out with people you've never heard of, calling you more often to see where you are and to ask when you're going to come home. They might be more critical, or they might emotionally "check out."

How should I confront them with my suspicions?
Wait until you piece together quite a few bits of information. People often want to confront immediately when they find one phone number or one letter, but show some self-restraint. A single thing is easy for the other person to explain away, but if you have four or five things — you overheard the phone conversations, you dropped by where he was supposed to be and he wasn't there, you've seen his car parked in front of his ex-girlfriend's house — that makes it tougher for them.

Can a relationship survive after someone's cheated?
Oh yeah, mine is a testament to that. A lot of times, when people start looking for evidence of cheating, it's not because they want to leave the relationship, it's because they want the other person to shape up. They're saying, "Hey, I'm onto you and we need to work together and get through this." But both people need to make a commitment that this is really what they want to do. They've also got to cut all ties to the person they cheated with. Keeping her around as a friend just isn't going to fly.

I just started dating again after getting out of a long-term relationship. How can I ease back into the game?
This is the perfect time to establish what I call my "Minimum Standard of Care." This is a check-off list you put together before you meet someone to identify the factors you are not willing to tolerate, because it's really hard to set those standards after you've had that first screaming orgasm. It's during this "me time" — between relationships — that you put that list together. "I will not be with somebody who is not religious." "I will not be with somebody who is a drinker." "I will not be with someone who has cheated in the past." These are things that are deal breakers for you.

Is it a bad idea to move in with someone you used to have a sexual relationship with?
Ha! That's like trying to put toothpaste back in the tube. From then on, any other person you date, knowing about your situation — it just has the makings of a bad scene.

When is break-up sex appropriate, and when is it a bad idea?
It's a bad idea when both people aren't in the same place. If you're still attached to this person and they're trying to move away from you, it's dangerous for both of you. But if you've both come to understand that you're going your way and I'm going mine, I have no problem with one for the road.

When should I discuss my past relationships with someone I'm dating? What should I tell them and what should I leave out?
Any pivotal points that brought you to where you are now are important to discuss, like if you were with an abusive partner in the past, or were with someone who cheated on you and that ended it. It's important to put that information out there early on so they can know what to expect from you. However, all of the nitty-gritty of who and where and how many — I wouldn't give up that information. My grandmother used to say, "Don't stir an old shit. It starts to stink."

Mark, 44

I'm sixteen and just lost my virginity to a much older man who I thought I was in love with. I now realize that it meant nothing to him and he took advantage of me. How do I get over a mistake like this?
You could have fallen head over heels for someone your own age and gotten just as hurt. Who doesn't make mistakes when they're fifteen? You're being way too hard on yourself. The real moral of the story is don't trust older men.

What are some clues that my significant other is cheating?
When most people lie, they don't deny reality completely. They just cut out the truth. For instance, if you were at a wedding and the bride was unattractive and she asked how she looked, you'd say you like her hair or that her dress is beautiful. So it's about being a good listener. Just like when you have surgery, it leaves a scar — when you do verbal surgery on a story, you're going to leave verbal scars.

Can a relationship survive after someone cheats?
The short answer is yes. But if you can't keep your legs together don't expect your partner to ever trust you again. I think it's clear that once you cheat the first time, the second time is easier. A lot of that guilt gets dispersed.

I just got out of a long relationship. Now I want to date several guys at once. Will this adversely affect my chances with all of them?
People love competition. If you let them know you're playing the field, the guys will pay extra attention. It's like when you're selling a car: you don't have one person come look at it at ten o'clock, one person come at noon and one person at two o'clock. You have them all come at noon and let them look at it one at a time while the others have to wait their turn. While the first person is looking at the car, the other two are saying to themselves, "I hope he doesn't buy it." It creates desire. That's human nature.

How can I recover from the social disaster of giving someone an STD?
You can't. There's no bouquet for that. Move away, preferably to a different state.

Dyana, 36

What skills does a private investigator have that can be applied in the bedroom?
We're role players. Our whole industry is based on pretending we're someone other than ourselves.

I'm seventeen and gay. What's the best way to tell my parents?
It depends on your relationship with them. If they're open minded you can sit down and tell them. If not, you need to go to your local gay community center, seek out some counseling and make an appointment to have a professional sit in on this, so they can address any issues that the parents might have.

What sexual skill do men most need to practice?
Foreplay. And foreplay of the mind, not just foreplay of the body. Romance isn't just dinner, flowers and candles. Support her, encourage her, compliment her and you'll get it all the time — anyway you want it.

What sexual skill do women most need to practice?
They need to open up. That same freaky shit you were willing to do to get the ring, you need to continue afterward. Chill out about wondering whether he's going to think you're a slut or a freak. Meet him halfway. It's true what our mothers said: "Men like a lady in the street and a freak in the bedroom." And if you don't know what a freak is, you have some girlfriends who do. Go take a strip class. Talk to a hooker.

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

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