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Sebastian, 31
www.progunprogressive.com


How can I have sex with someone once and never speak to them again without seeming like an asshole?
Geography is your best bet. It usually helps if you have a situational excuse to fall back on, like "I'm going out of town for a long time," or, "I'm just in town for the weekend."


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How long should I wait after a friend's breakup before I tell him I hated his girlfriend?
Thirty seconds. Maybe a little more. That's what they're looking for, a little affirmation: "You're better off without that situation."

I live with three people. What's the best way to get busy without my roommates knowing all my business?
Do it at odd hours in odd places. Everybody needs to take showers. And stairwells have always been good to me.

Is it ever okay to have sex with a longtime friend?
That depends. Guys don't tend to draw the same line between being friends and being a romantic interest as women do. With women, they call it the ladder theory I believe — they have a distinct group that they see as friends, and then they have people who they're ready to see as romantic interests. Men, we just don't draw that kind of dichotomy. If we're attracted, we're attracted and that's it.

How about sex with my longtime friend's mom?
Hot moms are definitely fair game. Just be prepared for the consequences.

What firearm-related gear could I incorporate into sex?
That's a tough one. A lot of the stuff that's useful for tactical wear is bulky and will obscure the body. But then, there's something to be said for a little mystery. A girl dressed in SWAT gear could be pretty sexy.

When you have a crush on someone, how long is too long not to make a move? At what point do you miss your chance?
What I've learned from being the nice guy is that you'd better strike sooner rather than later, because the longer it goes on, the further you get up that "friend ladder" and the more unlikely it is that the object of your desire will see you in a romantic light.

My girlfriend just told me she's slept with over a hundred men. It was obviously a big step for her to tell me. Nevertheless, I'm a little put off. Am I wrong for not being okay with this?
I don't think it's all right not to be okay with it. I don't think it's anybody else's place to judge. If it's upsetting to her, you need to confront her on why exactly she's upset about it, and make her realize she's just hanging a number around her neck that she doesn't need to.


Krikket, 35
www.pinkpistols.org


KrikketWhere's the best place to pick up a gun enthusiast?
Obviously at the local range or gun store, you're going to hit it one-hundred percent. But just like with anything, in a cross-section of Americans, gun people are everywhere — at your local grocery store or at the bar or what have you.

When is it okay to tell a friend that you don't like their significant other?
Here's an example from my past: There was a friend of mine who was getting married. I was asked to stand up at the wedding and say something, and I had my doubts. So I took him aside one day and said, "I have some serious concerns about this. Are you sure this is what you want?" He said yes. So I acknowledged his desire and shut up, and it's proven to be a very good relationship. The people in the relationship always know a lot more than you will from the outside.

When you have a crush on someone, how long is too long not to make a move? At what point do you miss your chance?
There are times when waiting just a week is too long and the person is going to lose interest and go elsewhere. That's happened to me. A friend and I had some sort of a thing and when she moved, I thought there was a lack of interest. I've now found out about ten years later that the interest is still there, and she's coming to town. So it all depends on the person.

What should I and shouldn't I ask my significant other about their sexual history?
I believe that no question is completely off-limits. I open myself up to any and all questions, and I appreciate it when my partner does the same. I don't want there to be something lurking that could pop up nastily in the future.

Is it ever okay to sleep with the sibling of an ex?
Is it ever okay? Yes. Is it necessarily the right thing to do? No. It depends on the people involved. It's a good idea not to run rampant over other people's emotions. If the situation can come about in a way where that doesn't happen, then have fun.

What rules should I lay down before starting a poly relationship? What needs to be said from the beginning?
You have to be honest, trusting and highly communicative. If you're none of the above, or if you're missing one of those three, then you have no business being poly.


Claire, "old enough to have done everything"
www.clairewolfe.com Claire


I'm going on a first date at a firing range and I've never shot a gun before. How can I avoid embarrassing myself?
First of all, if you're a woman going out for the first time, just relax — it's less painful than the first time you had sex. And if the guy that you're with — presuming this is a guy — makes it painful for you, then you know he's probably someone you should dump. If you're a guy going out with a woman, which could happen these days, don't pretend to know anything you don't know, because she'll eventually figure out that you're an ass.

Where's the best place to pick up a gun enthusiast other than the range?
Go to the gun store, especially if you're a woman. The guys there are so thrilled to see you come in the door that they'll do anything for you. Twenty years ago, a woman walking into a gun store would be treated like, "Well hello, little lady..." But now it's like, "Oh! A woman! She wants to learn to shoot! What can we show her?"

How soon after a friend's breakup can I tell him that I hated his girlfriend?
Right away. He needs to hear it so he won't be tempted to go back to her.

Is it ever okay to tell him you hate her while they're still dating?
Difficult, difficult. But you know, if it's a real friend, probably. He might beg to differ with you, but you're doing him a favor. Maybe he marries this woman and finds out ten years later that she's everything you thought. He'll listen to you one way or another, even if he doesn't take your advice.

What should I and shouldn't I ask my significant other about their sexual history?
Ask everything. I figure that grownups know that other grownups have had relationships, and you might learn something interesting about what your significant other likes or doesn't like, what they want or don't want.

What's the best way to handle getting caught cheating?
The best way to handle that is not to say, "I was just discussing special delivery with the mailman" or something. The best way to discuss it is to say, "Oh. Hi there. What do we do about this now?"

I'm a woman who's interested in experimenting with other women. A lesbian friend of mine told me to go for other curious straight girls because I'm liable to frustrate a lesbian. Is she right?
No, she's wrong. I think you should go for a real lesbian who can teach you things without you [and a straight girl] groping around in the dark like a couple of adolescents who don't know what they're doing.


Matt, 39Matt
www.liberalswithguns.com

My girlfriend and I moved in together too soon. Can I move out and continue dating her?
That's kind of a red flag. If a guy moves in with a woman and then wants to move out, that's an indirect way of saying that he wants to date other people. Women need to hold a guy's feet to the fire for that because that's just passive-aggressive bullshit.

What's the sexiest piece of shooting equipment?
Some people might find the brand new Smith and Wesson 500-caliber revolvers erotic. They have an eight-inch barrel.

My girlfriend just told me she's slept with over a hundred men. I'm a little put off. Am I wrong for not being okay with this?
Everybody has a past. But at the same time, it's like Reagan's mantra with the Soviet Union: "Trust yet verify." The guy has the right to be suspicious.

How can I keep money issues from mucking up my relationship?
From my perspective, a lot of men become resentful when the women in their lives have an unreasonable financial expectation. I'm married now, but when I was dating I was never offended by a woman who wanted to pay her own way, because then the contract is very clear. The woman is saying, "I'm not with you because I'm expecting a free meal," and the guy isn't thinking, "She used me, so she'd better go to bed with me tonight."

I'm a woman who's interested in experimenting with other women. A lesbian friend of mine told me to go for other curious straight girls because I'm liable to frustrate a lesbian. Is she right?
I think she's right. In my view you're either AC or you're DC, and both are fine. But if you're not really a lesbian — or in a male situation, if you're not really gay — your heart and soul are not really going to be in the act. If you're on the fence, wavering, looking to experiment, chances are the dyed-in-the-wool lesbian is going to know and you're not going to be able to please her the way another lesbian could.

How long can I wait before telling my crush I'm attracted to them?
Two weeks. There's no reason to hold on to something like that if you're not going to do anything about it.

Is there a way to have sex with someone once and never speak to them again without seeming like an asshole?
The only way I think you could do that is if you're paying for sex. Short of that, you're entering asshole territory.   


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


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