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Ashley, 25

I just started dating this girl a week ago and it's her birthday. What's a romantic gift that won't imply I'm gunning for marriage?
Something from Babes in Toyland. Keep it on a fun sexual tip but not super-emotional romantic.

I have a crush on a waitress at a restaurant. I want to ask her out, but I'm worried she gets hit on by lots of customers. How do I avoid coming across as a sleazy cliché?
First, you've got to tip her big to even get her attention. Then you've got to notice something subtle about her and let her know that you're paying attention to something other than her just being hot.


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I recently went on a first date, during which I accidentally got hammered and threw up in a corner while she was watching. How can I make up for this awful first impression?
Just tell her you had some bad Indian food and that you're really sorry about it. Say if you could take her out to dinner and drinks, you'd be much obliged. Definitely not Indian food, though, because that's what happens. Bad Indian food plus too much booze equals barfing every time.

I'm a bisexual woman. I recently broke up with a boy and I'm trying to meet ladies again. I went out on a date with a girl, but she seemed put off when I told her about my ex. What to do?
Keep your fucking mouth shut and don't bring up your exes when you're out with someone else. That's the cardinal rule. If you don't want to get laid, talk about your exes.

My boyfriend is in a band and I have a feeling he's sleeping with other people while on the road. How can I find out?
If you're dating a rock star, they're fucking other people. That's just a given. Unless he's really emo or something's wrong with him. Don't date rock stars, DJs, musicians, or artists. They're all sluts. But if you must, then try to deal with the reality of what's going on. Do a background check on MySpace or whatever stalker shit you've got to do in order to figure it out.

Besides the most obvious use of a pool cue, what's the best way to incorporate pool equipment into sex?
Instead of its most obvious use, a little spanking with the pool cue. I wouldn't mind smacking somebody around with one.

I asked the woman I've been dating about her sexual history, but she refuses to talk about it. Should I be nervous? Is she obligated to tell me?
You don't necessarily need to be worried, but don't ask questions you don't really want to know the answers to. Does it matter? Sometimes it's better if you just don't know. Then you'll have all this shit going around in your head — her fucking however many people. That's not necessary.


Danielle, 24

What's the best way to get a pool player go home with you?
That's a skill I'm still trying to master. For my friends, it's been the whole thing where they're good at pool and somebody else isn't and they're like, "Let me show you how to play pool." Pool is one of those things where you can get yourself into a position behind somebody as you're guiding their pool cue and accidental contact occurs and you can kind of work from there.

I love going down on my girlfriend and want to keep doing it, but she hates giving oral sex and I feel like there should be some reciprocation. Who's right?
Some people really like giving and not getting. And some people like getting and not giving, and that sucks. You can't really say, "I'm doing this for you," because you're doing it because you like to do it. Set time limits. Say, "Listen, I go down on you for really long stretches of time, so I expect at least three good minutes."

My best friend is married and has a baby. He recently told me he cheated on his wife. He's really torn up about it and says it will never happen again. Should I tell her?
I think you should. I've been a cheater, yet I support the idea of your friends telling on you. If my girlfriend's friends had known that I was cheating, I wouldn't have been pissed off at them for telling my girlfriend. I would understand why they did.

I asked the woman I've been dating about her sexual history, but she refuses to talk about it. Should I be nervous? Is she obligated to tell me?
I don't think anybody is obligated to tell you anything other than for health reasons. If they don't want to tell you then you just better wrap your shit up and take every precaution necessary.

I have a crush on a waitress at a restaurant I often go to. How can I ask her out without seeming a sleazy cliché?
Do something dorky, because either she's going to think you're really bizarre and weird or a total asshole. Personally I'd rather have people think I'm bizarre.


Kristin, 24

What's the best way to approach someone at a bar?
Go up to them and say, "Hey, what's your name, I think you're cute. Want to get a drink?" Then you get a drink, and after talking to them for a few minutes you say, "You know what? Want to make out?" That's the way it happens for me. Grow some balls.

I've been in a relationship for three years. I love my girlfriend and don't want to break up with her, but lately I can't get this girl in my yoga class out of my mind, and I think the attraction is mutual. Should I leave my girlfriend, or go with my impulse and sleep with yoga girl?
First of all, find out whether the attraction is mutual. Don't fuck up the relationship if you're not going to get any ass out of it from the other girl. Then hook up with the other girl, tell the girlfriend and gauge her reaction.

Besides the obvious use of a pool cue, what's the best way to incorporate pool equipment into sex?
Fucking on top of the pool table would be hot, but make sure it's not your pool table because you might fuck up the lining. Use somebody else's pool table who you're never going to see again.

I am a lesbian and I think I'm falling in love with my female friend. She's straight, but I think she once slept with a woman in college. Should I try to get her into bed?
You might be able to hook up with her, but you're never going to be able to get her to fall in love with you if she's really straight. Basically you're going to have sex, but it's not going to be good because she's not going to know what she's doing, and it's going to fuck with you for a long time, and then it will ruin your friendship. Stay away.

I love going down on my boyfriend and want to keep doing it, but he hates giving oral sex. I feel like there should be some reciprocation. Who's right?
You are. Tell him to get over it and lick some puss.


Lauren, 24

I just started dating this girl a week ago and it's her birthday. What's a romantic gift that won't imply I'm gunning for marriage?
Making a mix CD is always appropriate. It doesn't cost a lot of money, it's fun and doesn't connote anything serious.

I have a crush on a waitress at a restaurant I often go to. How do I ask her out without seeming like a sleazy cliché?
Get to know her first. I work at a restaurant. If someone is a regular and I get to know them, I won't consider them sleazy if after a while they ask about me. It's just about time and building a rapport.

What's the best place to have sex in a crowded bar, besides the bathroom?
In the back room, where they store the beer.

What's the best way to incorporate pool equipment into sex?
If you can get her up high enough, put a couple of the pool balls up against the woman's clitoris so it stimulates her as you're entering her from behind.

I'm really into using strap-ons but my girlfriend is weirded out by it. How do I ease her into it without freaking her out?
Just play with the strap-on in a way so there's no full penetration at first. Just wear it. Eventually she'll want it.

I love going down on my girlfriend and I want to keep doing it, but she hates giving oral sex. I feel like there should be some reciprocation. Am I right?
I think in a just society people who give should get, and if she's not willing to please you in that way, or in other ways, then you should move on. There are a lot of other people who are willing to please. 



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


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