The Perils Of Dating Old Guys


Once upon a time at a hotel bar in Santa Monica, I met a few middle-aged girls belly up and elbows deep in Chardonnay. I was a little down on my luck, but the girls reassured me that an executive class ticket to the good times was to find myself an older man. It was a sign I was still young and fabulous. I agreed. We shared a bottle or two…or three, and I closed out the bar with some guy in a striped monogrammed polo clutching my arm with one hand and downing his umpteenth beer with his other. His tolerance had gone to the dogs long ago, and my dignity with it. He told me I was cute. It had really come to this.

Old guys are smooth. They’ve got connections. More than you do, at least. You imagine the one who bought your last drink will sweep you off your feet and hook you up without expecting anything in exchange. Don’t feel bad: it’s a common delusion. After a few ill-fated dry runs in fast cars, too many winky face texts, and one poorly-placed comment comparing the taste of my lady business to his favorite sweet potato fries, I started to get the feeling that I needed to re-evaluate my game plan. Things just weren’t working out as the girls had promised.

I stuck to my guns for a while and tried out the whole “guys in their twenties” thing. My experiment resulted in plenty of convos about fantasy football, wild nights out, the screenplay he’s writing, and daddy issues. I was told that I would never know meaning in life until I pulled an old man from a burning building. I guess my life will be forever meaningless. As it turns out, the only difference between the young ones and the old ones is the wine is worse. Time passed and I chucked my conviction out the window. That’s when I met Rich.

I bumbled into this guy in the elevator at my condo building. Old enough to be my dad, Rich was a mile-a-minute talker/wheeler-dealer and couldn’t resist telling me all the interesting things about himself. We chatted for a hot second. He was quick to point out that he was having marital troubles and that later this week he was meeting Petra Nemcova to discuss his nonprofit. It was one of those confusing encounters where you aren’t sure that he’s aware you’ve never actually met, because he acts like he’s your BFF. Rich gave me his contact info, which was promptly lost in that “Notes” app I never use, and I figured this would be a classic case of awkward waves and passing conversations until he got the hint.

Rich was relentless. His advances were fairly standard. First came an invitation to dinner at the chicest place in town. Or more like a choice between the two chicest places in town. What? I only go there with my dad. I told him maybe not this time. Rich continued pursuing me like I was some sort of prize free agent. Lingering lobby conversations, uncomfortable clothing comments, and an unprecedented shirt-lifting incident in the garage, all in an effort to be smooth and seductive. I was embarrassed for him when he called me at work from the condo concierge to say “Hi.” Even more so when he suggested we run together. I run with my own crew and was not down to hang in the fat-burn zone with my neighbor. All of this was pretty much par for the course, until he showed up at my apartment door late one Thursday night. That’ll teach me to pick on guys my own size.

Complimentary, connected, and full of the promise of wining and dining at all those places I definitely couldn’t afford. Handsome, but in a sugar daddy kind of way. But for real, old guys are the ones scoring a first class ticket to the virginal world of pre-botox, perky boobs, and moving-forehead smiles. I stopped waving at Rich in the lobby and tried to avoid the building if I spotted him in the elevator. A few weeks ago I returned home from a run to find Rich hunched beside a Townie bicycle. A roller suitcase with a recyclable Whole Foods bag full of TP propped on the handle waited by his feet. In his arms he carried baby blue bed sheets and a matching duvet. Rich was moving out, and I’m just like, this fuckin’ guy…

When you realize being young, professional, and poor isn’t nearly as fun as being a poor college student, brainstorming get-rich-quick schemes over cheap whiskey and cheaper wine becomes a pretty enjoyable late-night pastime. Planning for the future with a future ex-husband is an age old fave for ladies the world over. Too bad it isn’t as easy breezy as it’s chalked up to be.

So for now, my Happily Ever After gets me punted me back out into the cold world of contract work and odd-jobs, drinking my dinner, and the interminable pursuit of “figuring my shit out.” Until I do, I’ve got a big girl vibrator and a second-to-bottom shelf bottle of wine. Clock’s ticking, and I plan on making the most of being young and fabulous.

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