Younger vs. Older Women

It's a well-worn cliche that when a man in his later 30s gets divorced, he starts going after younger women.

For my part, it's been almost two years since I was thrust back into the dating pool and I'm pleased to report that I have never, during this time, discriminated against any woman because of her age.

I'll be 39 in two weeks and I'm having more fun than I ever had at 25. At 25, I was pretty much limited to dating girls my own age. I went 5 years up and 5 years down, but that was the extent of my range. Now, I date women in their early 20's all the way to my own age and I wouldn't be opposed to going older if the attraction is there. A wider age range necessarily increases your dating opportunities.

Urban Melissa once kidded me about being "notorious" when it comes to dating younger women. I had to remind her that the majority of women I date are in their 30s. She agreed, but added that it only takes a few instances for a reputation to stick.

I'm probably a little bit sensitive about being seen as an old goat, but I have one tremendous advantage working for me: I've always looked very young for my age. At 25, it tended to be a thorn in the side of my ego; I could still pass for a high school student and it wasn't unusual, on a date with a girl my own age, for ME to be the one who was carded. Now, however, it's a compliment to be carded. I have a little bit of a salt-and-pepper look going with my hair but I've managed to stay fit, I still wear 32-waist jeans and I look about 10 years younger than I am. Whenever I'm asked how old I am, I usually respond with:

"How old do I look?"

The answers this year have ranged from 27 to 31. When I reveal my age, the reaction is usually,

"No way!"

Some 20-somethings don't go for older men. Plenty, however, do.

In these older-younger dating situations, both parties have to benefit for it to work. The older guy usually gets someone to look up to him and defer to him on account of his extended life experiences(didn't Kissinger call power the ultimate aphrodisiac(?) and, let's be honest, there usually will be a power imbalance here)and gets to benefit from the fashion advice and music recommendations a younger woman can provide. And firm breasts and asses unmarked by stretches are more likely to be found on younger rather than older women.

The younger woman gets a guy with an "adult" income who knows how to handle himself in a restaurant (gee, do I tip this guy? the water-filler? the guy who shows us to our seats? Can I just order a redbull vodka with my steak?) and is more likely than his younger counterpart to take her to places like the theater, opera, jazz clubs and concerts in the park. She also gets to enjoy the power of her feminine sexuality, or so I've been told by two women who have made a career of dating older men.

The downside, however, is also considerable. Younger women tend to be more melodramatic. There are more likely to cry and will do so more often than older women. They will probably have friends who wear their baseball caps backwards and arrive at parties on skateboards. The kinds of friends who don't shake hands when they meet someone because that's too old and square. And younger women may not understand that you have a big day at work tomorrow, hence your reluctance to go to the loud club with the awful music where the doorman has your names reserved on "the list."

You will not understand each other's cultural references. I have watched as old tag lines from Saturday Night Live have gone over some younger woman's head, and admitted to having no idea who John Legend was and been made to feel as if I had not heard of an entire world war.

The great advantage of dating older women, especially divorced women, is that they are more tolerant of male foibles. Having been around the block, they are less likely to foster sentimental images of white weddings and picket fences---images into which you are automatically cut-and-pasted. They tend to be more even-keel, and you will probably get along better with their friends. You will understand their 80s pop-cultural references, they will understand yours, and you will feel the comfort of generational solidarity.

The wild card issue is kids. For me, children are not necessarily a deal-breaker. A woman who neglects her responsibility to her children, that's a deal-breaker It's usually more convenient for dating if the kids are in their teens, or approaching their teens. If they are high-maintenance problem children, you probably won't be dating each other for long.

As far as sex appeal is concerned, a woman who knows how to use her eyes, radiates confidence and is comfortable in her own skin will be attractive regardless of her age.