Confessions of A Dating Dad

One man's quest to find a woman his own age.

By Tom Henderson
tom henderson
Photograph: Tom Henderson

There are jack-o’-lanterns from last Halloween that are wearing their age better than Hugh Hefner. 

They probably smell better, too. 

I look at the age difference between America's Original Dirty Old Man and his young lovers and, like so many people, wish something would finally shrivel up and fall off him so he can't gross us out anymore. Of course, he's not the first old coot to invite a young thang into his basement to dust off his antiques. Old men seem to have an affinity for young women. 

Not me. I confine my dating to women my own age. Maybe even a little older. This is not because Megan Fox's attorney tells me that Miss Fox finds fat, divorced 48-year-old men who get paid in Happy Meal coupons "creepy.” Still, it's true I am not the sort of older man who normally attracts twentysomethings. To play the gray fox, you need enough money to attract gold diggers, or need to find a mentally disturbed woman with "daddy issues." And Lindsay Lohan is just not my type.

My type is actually a lot closer to my age and hair color. That's because I am what you might call an intellectual. I want to be with a woman I can actually talk to before and after sex. Sometimes during. However, harsh experience has taught me that talking too much about Doctor Who during intercourse can be a real buzzkill. I swear I thought she said she liked "nerdy talk."
I understand the lure of young women. Gravity is still their friend. Their bodies are not all puffy and wrinkly like, say, mine. But unless you only want sex with a woman who is going to make fun of your body later on in tweets to her friends, you need to find someone you can relate to on an emotional and intellectual level.
Not that I have anything against middle-aged bodies. I love women in their ’50s. (You are listening, Katie Couric? Call me.)
But it's the mental connection that's most important. I need someone who will respond to my Jonny Quest references (and they are legion) with more than a blank stare. I have a hard enough time finding someone to relate to in my own demographic group.
A few weeks ago, I bought two tickets to a tribute to George Gershwin. I bought two tickets because, seriously, this is date bait. Who wouldn't want to go a tribute to George Gershwin? Everyone, it turns out. I wound up taking my 50-year-old sister, who went partly out of pity but mostly because of the chance to laugh at me.
We were the youngest people in the hall. "Good God!" said my sister (who once danced on stage with Lux Interior at a Cramps concert) as she surveyed the sea of white heads. "It's like being trapped in a $#@! Q-tip box."
She suggested I start cruising for chicks at the senior center.
Sigh. Maybe she's right. I do tend to have older tastes. Back in college, I couldn't understand why I couldn't find a girl between the ages of 18 and 22 interested in seeing James Whitmore perform his one-man show based on the life of Will Rogers. Women. Who can understand them?
My understanding has not improved with age. All I know is that my best shot at having a meaningful conversation with a woman is with one in her ’40s or ’50s—preferably with children. As a single father, I like single mothers. They understand conflicting priorities and the obligations of parenthood. They appreciate that you may have to cancel an engagement because you just paid $400 on your kid's braces, or that your next date might be dining at Applebee's instead of the local four-star restaurant.
Hey, coupons is coupons.
I rarely date anymore. I did the thing for a while after my divorce, frantically looking for a replacement part. I hated how online dating made meeting people about as romantic as Sunday brunch at Old Country Buffet. Don't like the chicken? Here, try the roast beef.
You don't have to commit to anything. Just keep nibbling.
I figure love should be a pothole you don't see coming. You go about your life, and if you stumble or fall in, so be it. I just hope I fall for someone my own age, because sex, really, is a minuscule portion of any romantic relationship. Most of a relationship is talking, sharing, relating—just being friends.

First Published October 10, 2011

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Olivia Lang10.10.2011

I absolutely love this article. Tom, how did we end up on opposite ends of the country? Ah well -- you really are the best, and I wish all the best for you.

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