Laurel, 20

What's the best way to pick someone up on Chatroulette?
It's all about first impressions. There has to be something about you that'll catch your beholder's eye, because you know their finger is already poised on the 'next' button. Find your best angle and flash a big smile. Or try dancing around.

What has Chatroulette taught you about dating?
It taught me that the most interesting relationships are often short-lived. You can't get discouraged when the person you're connecting with moves on to the next, there will always be someone else out there looking for the same thing as you.

I'm in a monogamous relationship, but I like jerking off with people over the internet. Is this cheating? Should I tell my partner?
Definitely don't tell your partner. You are creepy, and if they haven't figured it out yet, telling them is just not going to help the situation. In a world where technology is rapidly changing our social mores, it's hard to say if this is cheating. Let's just say what happens on the internet stays on the internet.

My girlfriend says I suck at going down on her. What should I do?
Make some lesbian friends, read some erotica, pick up Cunnilingus for Dummies. WikiHow probably has an article on it. Just don't keep trying, it won't be fun for anyone involved. You can try to ask her what she likes, but remember that girls don't like to tell you what they really want.

I want to tape my boyfriend and I having sex; how should I bring it up?
He hasn't asked you yet? You shouldn't be too worried he'll turn you down, but this is not something that should be talked about anywhere but the bedroom. Leave the video camera in there next time you two are going to crack open a bottle of wine. He'll get the hint.

Is texting an acceptable way to cancel a date?
OMG yes. Regardless of your reasons, this conversation is going to be awkward. Be a real asshole and try to keep it under ten words. Don't bother to spellcheck. In fact, don't even spell out the word 'you'. And definitely don't apologize. You should probably do it on Valentine's Day.

Do I sound bitter?

I just found out my current girlfriend and my ex are casual friends. The last relationship ended badly. Should I bring this up with my current girl before the ex does?
Did the last relationship end badly because of something you did? You should probably find a way to start some drama between the two girls before your ex finds out you're dating her friend. Or you could always try apologizing to your ex and mending that relationship so that you can both move on.