The Hook Up: 4-13-2011


I tend to have a thing for older women. My longest relationship was with a woman who was 13 years older than me. Once my ex (who was roughly the same age as I am) broke up with me, an older woman friend one day surprised me by kissing me. I had never thought of her in this light until she did that and now it feels like she’s simply teasing me. She is the kind of hot/cold/hot/cold that would drive anyone nuts. I have, however, developed quite a crush on her.

My best friend is of the opinion that I only do this because I like to chase. When someone is interested and available I am not likely to jump on the bandwagon.

I do rather like my freedom but do you think it’s about wanting the unavailable or simply not wanting to compromise my freedom? Or is it just my thing for older women? And if it is, why do I like older women so much? Is it a problem? Can it ever really work out with an older woman? -The Graduate

Anna says: Chasing can be a lot of fun, especially when you’re recovering from a break up. It’s a nice distraction, but one that doesn’t usually require a huge time-commitment, like Angry Birds or prison. If you want to pursue something with Ms. Hot ‘N Cold, then I’m not going to talk you out of it, so long as you’re not doing so with the realization that she will probably not turn out to be your eternal soul mate unicorn at the end of the double rainbow. If you don’t mind the cat-and-mouse routine, if you enjoy her company and sweet kissin’, and perhaps most importantly, if you don’t mind the possibility that your friendship will be forever altered (and not necessarily in a good way), then by all means, go git ‘er.

As to the liking unavailable women theory, I’d trust that your best friend knows you better than I do, but I will say that wanting what we can’t have is as common as it is for Kanye West to tweet in all-caps about his frustration with finding PERSIAN RUGS WITH CHERUB IMAGERY. Several of my friends have said the same thing about me. And I’m like, just because I’m in love with a girl who lives across the country and has a boyfriend doesn’t mean she’s unavailable! And then someone pats me on the head and gives me a Snickers bar to quiet me.

Oh, those delicious taboos. We love them. They’re hot. That’s one of the thrills of being queer too. We bust cultural expectations simply by being who we are. The danger in pursuing unavailable women is when it starts to become habitual. If you’re turning down a date with the hot, quirky barista simply because she’s single, then you might want to reexamine your priorities.

However, I think we also tend to chase after unavailable women because we aren’t necessarily in a place where we want to settle down. And that’s OK. Friends are quick to point out patterns in our love lives — Curiously, these friends are often happily coupled — but patterns don’t always mean anything, nor do they have to become self-fulfilling prophecies. I’ve dated a crap-ton of Sagittariuses and almost all of them have been in love with Amanda Palmer. Is that a pattern? Yep. Does it mean I am doomed to forever live in the shadow of Amanda Palmer’s awesomeness? Probably. But it’s not the world’s biggest deal breaker. If they were all in love with Gary Busey or something, then I might worry. That said, I think you have a crush on this lady because you know she’s into you, at least somewhat. I mean, she did kiss you. You can’t get much more obvious than that.

As to your preference for older ladies: What’s not to love about them? They’re more experienced, they know what they want, are often more stable, and their meals rarely ever involve the words “spray-on cheese.” May-December relationships, or in your case, Gay-December relationships, are just as likely to be long-lasting as ones without a significant age-gap. However, one potential pitfall to avoid is constantly referencing your age difference. It’s one thing to gently poke fun at an elder for loving the Bee Gees, but quite another to say things like, “I lost my virginity when you were still in diapers.” No one needs that imagery. Oprah agrees with me on this one, which is a good thing because it’s necessary if we’re going to take our relationship to the next level. What was I saying about liking unavailable women again?

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