Dear Wayne and Wanda,
I have been single for a while and am OK with that. Things with my last boyfriend ended badly and I figured it didn't hurt to take a little time off from the dating world. But there is this guy -- we will call him Chris -- whom I have had this long-running flirtation with. It started when we met a few years ago. He is a bartender at a popular place downtown. We eventually became Facebook friends and then I gave him my number and we started chatting and texting more and more. He is easy to talk to and extremely cute, and he makes me laugh. Lately he's been asking if I'd want to hang out sometime and grab a drink or something. I know exactly what he means when he says "or something."
Problem is, he's 24. I'm 36.
I feel really weird about this age gap. I brought it up once. He asked how old I was, I told him and he said he didn't care. Is that really possible? I mean, I'm not a bad-looking girl but I'm not a supermodel, and he's an adorable bartender who no doubt has dozens of cute women his own age he could spend time with.
I guess I wonder if I should just end it now or let this keep going. Twelve years just seems like so much of a gap, but then again, we do get along great … And I can just tell from the crazy chemistry between us that we'd have a lot of fun. Help?
-- Mind the Gap
First off, if you were a guy interested in a younger woman, I don't even think we'd be having this conversation. Despite age-barrier-breaking vixens like Demi and Madonna, our society still loves to catcall a cougar. Well, screw them. We are women, hear us roar, and if you want to roar your way into the younger pants of a hottie bartender -- well, as those Nike folks say, just do it.
But don't do more than that. Enjoy the cute dude, have your fun -- maybe have it a few times -- but know that he's probably not looking for much else. That's exactly why the age gap doesn't matter to him: He isn't seeking a soul mate, just someone to mate with, and as an attractive older woman, you're satisfying one of the basic male fantasies (more experienced older woman, "Risky Business," etc.).
Have your fun and get it out of your system. Also, be prepared for the fact that if you do sleep with him, the flirty banter, texts and chats may fade away. He will, after all, have finally landed the cougar he set about hunting a few years ago.
Roar! Watch out for the claws on Wanda!
It's totally true -- young men will flex their muscles and machismo to impress sexy older women, and older men will wine, dine and throw down the platinum card to get the attention of hot younger women. But this isn't exactly a May-December relationship we're talking about here. More like May to July. You might be old enough to be the big sister he never got to hang out with, but you aren't old enough to be his mom. So I'd say get over the age difference hang-up because I doubt he even cares.
Let's think more personally and selfishly. Your current period of reflection and rebound makes this a perfect time to explore opportunities to "have a lot of fun." Fun! No commitments! No overthinking things! You might be 10 years into your career and he might be charming lushes for dollars, but who the hell cares? The attraction between you two is mutual and it is electric.
So go with it. You deserve it and he's flirting his butt off for it. Have a good time and see where it goes.