Jenessa, 25

What's the best way to pick up a bike messenger?  
I don't know if I can tell you the best way, but I can tell you the worst, which is when people come up to you and say "Oh, so you're a bike messenger," and they get kind of cheesily star-struck and try to ask you weird shit about it. The best way is just the same as with any human being — be cool, be yourself, and don't try too hard. 
 
What's the best reason to date a bike messenger?  
We're good on the street, so we'll be good in bed, right? We're all adrenaline junkies. We're kind of wild, so we'll be crazy lovers. You can take care of us because we have no money. And we're kind of a family, so we have a lot of community and a lot of friends and there's always something going on.  
 
What has being a bike messenger taught you about sex?  
Take chances. Being a bike messenger is kind of scary sometimes, but you just have to do it. You've got to take chances in sex if you want to have really good sex. You have to take chances on the street if you want to get it done. And pedaling faster is not always the answer. 
 
My boyfriend doesn't ride a bike, but I ride everywhere. I think he may be afraid to ride. I'd be willing to teach him, but am tired of saying, "meet you there." How do I get him mobile without embarrassing him?  
Tell him it's a way to save money—  it's $2.25 a swipe on the train — and also a good way to stay in shape. Why wouldn't you want to? I'd play it on the sly and tell him, "You look really sexy on that bike," or "I really like it when we ride together." You can kind of pad his ego a little, Pavlov's-dog style. If he really doesn't want to ride a bike, I'm going to go with Dan Savage and say DTMFA.  
 
I don't like going down on my girlfriend, but she's really into it. Everything else is going great; is it fair for her to break things off because I don't do oral?
What is your problem, dude? No one loves having a cock in their mouth. Well, some people do, I guess, but if you really care about the person, you make a little bit of a sacrifice. Whatever your hang-up is, she's putting her face on your cock, which I think is worse because guys sweat more. If she's willing to go down on you, then come on, man, a vagina's not that gross. Think positive. 
 
My girlfriend wants to cut her hair short, but I really like ladies with long hair. I know it's ultimately her decision, but I think as her boyfriend I should have some say. Am I being a controlling prick? 
Yes, enough said. It's the twenty-first century — we're all equal here. Let the woman cut her fucking hair. 
 
I've been seeing this guy casually for a few weeks and I think I really like him. He just let me know that he has genital herpes. I appreciate his honesty, but I don't want to get infected. Is it fair to break up with someone because of a medical condition? 
You're probably not going to be with him forever, but you will have herpes forever. If you really like the guy, consider sticking it out. If you think it's going to be a fling, then why put yourself at risk?