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

Tags Infidelity

Commentarium (27 Comments)

Jun 08 11 - 2:21am

Julie's the best. I say insightful questions can be better than answers. Besides, they're fucking funny.

Jun 08 11 - 3:26am
"Too nice..."

has got to be a euphemism for something else like, 99% of the time. I got that a lot when I was younger, and you know what made me suddenly not TOO nice? Losing 25 pounds. My friend who still is "too nice" is actually just a socially retarded individual whose sister still does his laundry and who rambles on about work.

Unless two people have been going out for a really long time and have invested a lot in each other, they aren't going to get into the big issues. No one is going to say "I think you lack ambition and it affects your outlook on life," for example, if you've only been dating for a few months. They'll just look for the easiest out.

Jun 08 11 - 9:44am

"Too nice," in my world, usually means "too passive," which often, in turn, means "too chickenshit."

Jun 08 11 - 1:40pm

Agreed. It could really mean anything -- "bad in bed," "unambitious," "unintelligent," "unfunny/doesn't get my sense of humor," whatever. And congrats, "Too nice...", on not being one of those incredibly infuriating guys who has a girlfriend that tries to soften the blow of the break-up and then jumps on the internet to whine about how "women just don't know what they want!!!!!"

And an even heartier congrats on losing 25 lbs. Well done.

Jun 08 11 - 8:11pm

yep. or that the guy is JUST nice. He's really really nice, but he's not particularly charming or funny or smart or interesting, he's just...nice.

Jun 08 11 - 3:32am

For comedians, they're not very funny. Well, Julie is , but Cait of Miss Information is still a lot funnier.

Jun 08 11 - 1:40pm

Andrea was trying so hard to be funny it was embarrassing to read.

Jun 09 11 - 11:41am

I didn't really get that vibe, more just like good natured?

Jun 08 11 - 5:03pm

Cathy Ann is cute.

Jun 08 11 - 5:36pm

what . . . none of them were funny, Nerve

Jun 08 11 - 10:21pm

Julie, I wanna be inside you

Jun 09 11 - 11:46am

Too late dude. I'm in lesbians with her.

Jun 09 11 - 9:48am

Carly Ann - love your eyes

Jun 09 11 - 11:47am

Andrea is my favorite. Most definitely.

Jun 10 11 - 10:02pm

Remind me never to ask advice from Julie. Kind of a wench. Plus, the advice sucked.

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It's much easier to undesratnd when you put it that way!

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