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  • Writer's pictureLeah Jones

Sex in The City Moment–Does Age Matter?

I feel like Carrie Bradshaw this morning–writing a new column about dating in the city. My city, of course, is Chicago and I don’t meet my men at performance art shows, but online.

I mentioned that I posted Craigslist Ad #3 last week. Every ad gets more specific and this was my first ad asking that the men be Jewish. I also said that if I wouldn’t respond if you had answered to my ad in the past and answered with the same text this time.

Well, I got one repeat response–but his text was different and I could tell it was an authentic response and not just a blanket “I respond to every single ad on CL and have no life outside of this website.” I wrote him and said that I recognized him, he’d written before, and he was the one who quit writing me.

He remembered me and said he’d only ever answered 5 ads. Since I was 2 of the 5 ads he’d answered, he thought we should go ahead and meet. We scrapped our saturday night plans and met last night after we were both finished with work.

I kept it on my turf and we went to The Daily. Lucky for him, we had the new waitress. It isn’t just Tommy that knows my order, but now two other waitresses do. The conversation was easy and we have a lot in common–music backgrounds, jobs we love, travel stories and the jewish thing.

The thing we don’t have in common is age. I don’t know how much older than me he is, but my educated guess is somewhere between 10 and 15 years. I’ve always been okay with dating older men, but usually hovered around the 4-6 years up. My brother is 6 years older than me, so it seemed like a nice artificial break. Older than my brother is too old for me.

But then I dated BlogReader in London–he was about 10 years older than me. It was fine except for his constant comments about things I probably couldn’t remember or relate to, because I was so TERRIBLY young.

So that turned me off a little… a lot. But then I think of my guy friends who are in their older 40’s and ask myself, “If he was single (or single and straight), is he someone I would date?” And the answer is absolutely. I know pletny of men in their 40’s that I consider dateable.

If I hear from him, and I think I will, I’ll take him up on a second date. So far he’s been nothing but nice.

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