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.
Not at dinner! Don't say it at dinner. Please promise me you just won't say it then. Also, I don't know if you have to even say it. I think maybe people make a bigger thing out of losing one's virgnity than we have to, especially for girls — because there's a hymen involved and because we're told it's such a gift to have an un-popped puss and no sexual technique (fuck you, lingering misogynistic ideas about female promiscuity). Maybe it would be freeing to hide the fact that this is your first time, especially since sex, at its best, is a way to escape self-consciousness.
Also, women are weird about doing it with a guy who's never done it before, as I'm sure you know. Not that we should be, but if you want to have sex with this woman, I think you should do whatever you can to make sure that it happens. If you have to be totally honest about it, then I'd say tell her right before.
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?
Why do you want to know? Why would you care? Honestly, I'm not judging, I'm just baffled by that desire to know exactly how many women your boyfriend has slept with. Why would you tell him how many guys you've been with either? Is it competitive? Sorry to answer your question with ten-thousand questions of my own, but I really don't understand your motivation here.
What's important to a relationship is the two people who are in it. Who cares about what's in the past, as long as both of you are healthy? Do you think you might be dwelling in the past for other reasons? Oh, now I'm asking you stuff again. There is an excellent chance I am lousy at this job.
But my advice is, move on, ask him other stuff. What kind of animal would he be if he could choose? I would be a manatee. They don't do shit and they move real slow. And they've got cute faces! But they do get hit by boats.
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.
I hate to be the bearer of bad news, but I don't think she's going to want to ease up. And you're not going to grow into it. Either you guys figure out a way of doing sex to each other that both of you enjoy, or this isn't going to last. Sex isn't everything in a relationship, but it's important enough that when styles are incompatible, it can be a big problem. So either find a compromise or alternative to the rough stuff, or give it a matter of time.
I've been dumped at least three times for being "too nice." All my women friends tell me they want a nice guy. What the fuck?
Yeah, we mean "sweet." We actually want men who are confident and charming — aim for that. I mean, don't be a dick. Stay warm. Just, also don't apologize too much, or go for the whole stammering nebbish thing — Zach Braff killed that, then pissed on the corpse. Watch some old movies — Humphrey Bogart is a great example of how even without movie-star good looks, cynical, cool, funny, and guarded totally works.
Stay kind, stay open, but know that women are attracted to men who project ability, status, and strength. Don Draper is a whole thing. He's a pig, I know. Don't be a pig. But don't bend over backwards for women, either. I'm not saying be aloof — I hate aloof, personally. But try not to meet us more than halfway, at least when you're just starting to get to know somebody. It affects our respect of you, and respect is a big part of female desire.
I'm dating a girl who is very prim and proper, but has a reputation among my 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 myself — am I a freak-repellent?
I'm kind of skeeved out that your grapevine of friends gave you the hard sell on your new girlfriend. Is that a thing? Are girlfriends like businesses on Yelp now? I also think it's totally weird that you're all "so what" about the incestuousness of your group of friends, and that — in addition! — you are skeptical of your lady not delivering on their hive-mind expectations. If you're not satisfied with your sex life with this woman, that's between you and her. That can be ascribed to chemistry, mood, any number of things. Don't drag your pals into the conversation, unless you guys are orgy buds, in which case, again, I don't know what to tell you.
I just moved back in with my parents. Is it all over? By that I mean my sex life.
The bright side is, maybe you'll go out more, and that can always lead to sex with people. Also, it's a shitty economy, and people can be more understanding than you give them credit for, as long as you get to know them first so they're like, "Oh, this person is super sweet," before they find out you live at home, because it's easy to judge somebody when you’re first getting to know them, and harder to dismiss people as you realize they're more than the sum of their parts. To that end, maybe the new living arrangement will keep you honest, or make it so you won't hook up with people you randomly meet right away? Or, maybe you'll just go to theirs instead. Just don't lie about it, and try not to make complaining about your living situation "your thing." In the grand scheme of things, there are way worse fates that people have to deal with than a roof over their heads.
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? At night as well?
You mean "...til he leaves, to bone"? I don't think so, as long as you're quiet and he's not in the same room while you are boning.
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?
Is this a huge problem? Come on. You know it's worse when you want something serious and the other person is blowing you off. Either tell him that's what you want, or don't lead him on anymore. Call me when you've got real drama.
Julie Klausner is a writer and comedian in New York City. Buy her book, I Don't Care About Your Band, here. Listen to her podcast, How Was Your Week, here.
Photo by Ari Scott