Sex Advice From Female Comedians

Carly Ann Filbin

I have a personal blog, and I tend to go in details about everything sex-related. I love it, and I never use the guys’ real names. But my current boyfriend is extremely uncomfortable with it, and doesn't want to be included at all. He's a huge part of my life, and I want to write about him. Is he being unreasonable?
I see his point, and that’s a very tricky part of dating in the modern age. But if he knew you had a blog when he started dating you, he should be supportive of you. If this is something you really care about, and you’re not using his real name… you just need to make sure he knows how important it is to you.

I'm older and very inexperienced. Okay, I'm a virgin. I'm getting serious with a very special woman, and I'm ready to just do it already. But how do I break it to her? At dinner beforehand? Right before we're about to do it? I'm hung up on logistics.
It shouldn’t be a big event. It shouldn’t be built up! The same way “I love you” doesn’t have to be an important event. It can be a casual conversation. The more you try to make it a super-important conversation, the more awkward it will be. It’s normal thing. I know you might be freaked, but just try to be nonchalant about it. If she’s a cool girl she won’t make a huge deal about it.

My boyfriend's told me his number a few different times, and each time it's different. Insanely different. I won't think he's a skank or a prude — I just want to know the truth. I've been honest when I told him how many guys I've been with. Is it immature to keep pushing for it?
I think it’s shitty that he’s not being honest, but at the same time, it’s pretty immature to push for it. He could just tell you that he doesn’t want to give it, and you should respect it. Whatever the number is, it’s in the past, so I think you have to just let it go.

My girlfriend likes it rough. Like, really rough. I'm kind of uncomfortable with it. How can I get her to ease up on the rape fantasies? I'm just not into it.
Definitely communicate that verbally to her. It’s a give and take — half of sexy time should be whatever she wants and half of sexy time can be what you want. It’s a fairly simple solution. And it’s a blessing to find a girl who likes it rough.

I've been dumped at least thrice for being "too nice." All my female friends tell me they want a nice guy. What the fuck?
The fuck is: women want a nice guy when they’re in a relationship, but not too nice of a guy. They want to feel like they are working for it a little bit, and especially at the beginning of the relationship, a guy can’t be too nice or too much of a doormat. It’s the rules of attraction. Also, the real reason might not be that you’re too “nice,” but that you’re nice enough that they don’t want to tell you the real reason.

I'm dating a girl who is very prim and proper, but has a reputation among friends (we're an incestuous group, so what?) for being a freak in the sheets. I have yet to see the freak side. What's going on? I'm a pretty conservative guy — am I a freak-repellent?
It could be that you bring out a different side of her, and that’s not a negative. If you really want to see the freak side, you have to ask for it. Everyone has different sides of themselves in bed, and if that’s what you really want, you can’t shy away from talking about it. Why don’t you initiate something weird? Why does she have to do all the freak-work?

I just moved back in with my parents. Is it all over? By that I mean my sex life.
It’s definitely a killer, and it can put you in an awkward situation when you always suggest their place. But also, it could make a woman feel safer, with the parents around. But don’t fret, you can play it like, “Hey, we can go back to your place if it will make you more comfortable” and then you get to feel like an independent adult at her place.

A question of etiquette: I have a temporary live-in roommate. He's here for a month. Is it expected that my girlfriend and I wait til he leaves to have sex? At night as well?
No, it shouldn’t be expected, but also you’re being a host. You’ve invited this person into your house. Try to be quiet, I guess — it’s rude to make a lot of noise.

I hooked up with a guy when I was drunk and desperate, and led him on because I'm sure there will similar circumstances in the future, and he's kind of fun. But he wants to date, and take things seriously. How do I let him know I just want a friends-with-benefits relationship?
Just be honest: you’re not into having a relationship right now, but you want to explore and see how things go. It’s not lying, and it’s not mean. Some people just aren’t relationship material, for whatever reasons, but as long as you’re on the same page, you don’t have to feel bad about it.

Carly Ann Filbin is a comedian living, lusting, and lunching in New York City. Her improv team, COACH, hosts a show the second and fourth Saturday of the month at Triple Crown, and she enjoys run-on sentences.
Photo by Ari Scott