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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.

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