I am closing in on 30, and I’ve been single for all of my twenties. I’m pretty sure there’s nothing that makes me undateable: I’m friendly, social, intelligent, and averagely attractive. I’ve been on dates, but I’ve never pursued a girl or been pursued by one. I’m waiting to meet someone that I have to have. I’ve tried online dating, and had a lot of sex, but no relationships. What else should I be doing? Ten years alone is too much.—Joe
It is too much, and it’s likely to continue unless you really try to change your situation, because the longer an adult man (or woman, I guess, but I’m mostly privy to the whispery sacraments of straight girls) is single, the harder it is to not be. Women will find out immediately what your rel-ship history is (that’s how we talk about it on Gchat: “rel-ship history”), what your longest rel-ship was, who it was with, and why it ended. That’s just basic recon for a potential girlfriend. But because you’re not even 30, you still have a few years before a slim dating resume is going to become a self-perpetuating deal-breaker.
So what’s wrong with you? I asked Justin Halpern, who is the author of I Suck At Girls; he—or his father— is also responsible for the Twitter account-cum-book-cum TV show Sh*t My Dad Says. Considering that you’ve never pursued a girl, or had a girl pursue you, he asks, “How in the hell have you managed to have all this sex, then? Women are fairly picky about what penises they’re going to allow near them, so to have had a lot of sex, you must be either really good looking, super charming, or paying for it.”
He’s right, so you might just have unrealistic expectations, and not enough experience to know that you have them. Very few relationships begin with that feeling of need; usually it comes later, like at a red light while you’re arguing about disco. “You’re not going to bump into someone on the street, spill your coffee on them, and then get on a plane to meet the in-laws,” Halpern says. “Don’t count somebody out because they haven’t knocked you off your feet. Unless there is no physical attraction there, you’d be surprised how getting to know someone can make you much more into them.” Trying isn’t the same as settling, so the next time you go on a date, don’t evaluate it right away (and don’t have sex right away, either, because that has a tendency to short-circuit a new thing). Just go out, then go out again. Ask questions, don’t overanalyze, and do something with a girl that you’ve never done before. Ride Leviathan at Wonderland, eat Ethiopian, rent a canoe—anything corny will work.
“Stop putting so much pressure on yourself,” Halpern says. “Believe that you have options, and you’ll project confidence, even if the only option you currently have is an internet connection and a bottle of lotion.” When you date without panicking about what it isn’t, you’ll definitely find out what it is.
My housemates, who are best friends, are messy and inconsiderate. I’m sick of doing chores myself, or leaving their dishes to rot on the counter. How can I hold on to my sanity?—Sheena
Usually, I’d say something like, “talk, communicate, share, schedule!” or whatever. Living with two hardcore best friends, though, is worse than living with a collection of randoms, where you can at least find some rogue-agent clean-kitchen allies, and even worse than living with a couple, because usually one of them is already pissed at the other for being domestically retarded. But super-exclusive besties, especially when they live together, are like the messiest Lost Boys on never-ending no-sleep sugar-highs; your needs as an outsider aren’t going to penetrate their candy-coated BFF shield. Give up. Get out of there as soon as possible. Oh, and PS? They’re talking smack about you right now.
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