Bachelor #37

Everyone always tells me to be open-minded. Expand my horizons. So when Bachelor #37 wrote to me, I decided not to immediately dismiss him based on the fact that he's 53. In case somehow you missed it, I'm 40. And I usually adhere to a 10-year cutoff.

But Bachelor #37 was that elusive breed of Internet dater that doesn't post a picture not because he's all too keenly aware that he'd NEVER get a date if he did, but because he's just so darned successful and high-profile in his career that a little discretion is in order. The fantasy that men like that are out there is what made me try the whole Internet dating thing in the first place. When someone writes to me without a picture, I always think, he must be a politician or a prominant lawyer or maybe Patrick Dempsey. (Yes, I know he's happily married but this is my fantasy, OK?) Then, sure enough, he sends me a picture and it turns out he's a bald, toothless, cross-eyed maintenance manager at a nuclear power plant.

But Bachelor #37 sent me a few pictures and they were all pretty good. Turns out, he was a successful downtown trader, so he suggested we meet for a drink at the bar in one of the most expensive restaurants in the city. Naturally, I assumed if all went well we'd be staying for a lovely $300 dinner. After all, he chose the venue.

When I got off the elevator, there was this well-dressed man who, from the neck up, looked just like I thought he would. A little older, yes, but in a sophisticated kind of way, and quite a nice face.

The thing is ... and you know there's always a thing... in my indecision over whether or not to go out with a 53-year-old and my excitement at the notion of dinner with a successful trader, somehow, amazingly, I'd completely neglected to check how tall he was. I know, I know, I of all people should know better. So I guess you won't be surprised when I tell you that, in my 3-inch heels, I could see the top of his head.

But I guess HIS initial opinion was a little better, because he did suggest we stay for dinner. Funnily enough, sitting down he was so much more appealing. He was smart, and nice, and VERY interested in being in a relationship. Then he thought it would be nice to show me his office. Which meant, unfortunately, walking around together. And there was the top of his head again.

For the record, I did go out with him a second time. He was very nice and very interested, and I don't like to think I'm so shallow as to dismiss a perfectly reasonable candidate just because he's 5"6. But then on our second date, he wore a form-fitting t-shirt, and now in addition to seeing the top of his head, I could also see his 53-year old body. Is it shallow to want to want to see your man naked? There's either chemistry or there isn't, right?

Why can't I just ignore this silly desire to want to actually fall in love with someone, and just be a shameless gold digger and latch onto the next successful man that comes along? So what if he's short, he can always stand on his big fat wallet, can't he? And if I don't want to see him naked, can't I just keep my eyes closed? Who's to say the life of a gold digger isn't a happy one? Even if I wasn't in love with my husband, I would be madly in love with my shoes. Surely that is fulfillment enough?

But no. And so...

Next.