Julie, 40
I'm dating an older woman. I'm twenty-two and she's thirty-one. We have great chemistry, but she's worried about the age difference and thinks we should break up. But we always end up back in bed together. What should we do?
When a man says to a woman, "We should break up for both our long-term sakes," this means, "I don't want to have babies with you." When a woman says this to a man, it means, "I want to have babies, but not with you." You are twenty-two and have zero business having kids. You say you have great "chemistry" (hot sex) with this woman, but you don't say you're in love with her. Do her a favor, and let her go. Maybe you can be her tennis instructor or cabana boy once she realizes how utterly bored she is in five years.
My boyfriend and I go to different colleges. We've been dating for a year, but he still gets insecure when we're apart. He calls and texts constantly, and is suspicious of any guy friends I make. I love my boyfriend, but his insecurity is driving me away. What should I do?
Dump him. Now. Does he ask you what you wore today and who you talked to? I had one of those. (Hi, Dan!) Do not burn nine fucking years of your hot self on this guy when you could be out there meeting someone else.
I love my girlfriend, but her fashion sense is killing me. She's old enough to dress like a woman, not a rainbow-drenched scenester. How can I tell her without coming off as a superficial jackass?
Convince her that you have a fetish for evening gowns or business wear and ask her to dress up for you. Make sure you go on and on and on about how hot she looks and how much it turns you on to see her dressed this way. You might still come off as a superficial jackass, but most women are more tolerant of sex-related jackassery than guys telling us how to dress.
She swore she came twice. But we were drunk and she was dry the whole time. I'm coming off a long dry spell, and in spite of what she said, I'm afraid I've lost my touch for foreplay, which doesn't help my confidence now that I'm trying to date again. What should I do now?
Tell her you had fun but you'd like to try it again more sober. If she declines, you will know she was lying about getting off. No woman is going to turn down someone who can make her come twice on the first try — drunk, no less. At the very least, if she says yes, you'll have a second chance to achieve something better than sloppy, drunken sex. If she says no, try to be sober(ish) with whatever girl you end up with next time.
I've been dating this girl for six months, but she just issued an ultimatum: either I give up weed, or she gives up me. She doesn't smoke, but I never knew it was such a big issue for her. We're totally compatible in every other way, but now I think that she may not appreciate who I really am. What should I do?
Well, maybe the next girlfriend will love the ganja but not be willing to shave her cooch or her legs because "you're a pig for even asking." Yeah, there are chicks like me who have brains and are well-groomed and dirty in bed and smoke dope with abandon. But we're pretty rare, and when you meet us you're too fucking intimidated to date us, so figure out what you can deal with in a normal girl. And, before you give up all hope, find out what bothers her about the weed. Maybe it's the smoking aspect, and she'd let you chow down on pot brownies once in a while?
My boyfriend and I get along great — the only problem is, he doesn't talk when we eat dinner together! How can I teach him the art of conversation?
I suspect you're one of those chicks who just yap-yap-yaps all the time, and men deal with this by saying nothing, tuning you out, and waiting for you to get bored of talking to yourself. I'd suggest shutting up and letting him initiate the conversation. He probably won't do this the first night or the second night, but after five nights of silence, I bet he says something. If he doesn't do it, then he doesn't want to talk with you during dinner.
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