Dating an Older Guy: Like a Vacation... But Not

Fool me once, shame on you. Fool me twice, shame on me. Fool me three times — OK, what’s the lesson I’m supposed to be learning here?

Thus has gone my love life in the past eight months, the stars aligning to send me three 30-something guys in a row, all of whom stuck around for three or four good dates, only to fade into the background as swiftly as they emerged.

Dating these 30-something men as a 20-something woman was kind of like traveling abroad — foreign, fun, and fancier than the comforts of home. They all had interesting, established careers, nice apartments, preferred a higher grade of alcoholic beverage, and were well-traveled. “Established,” “high-grade,” and “well-traveled” are not modifiers of my 20-something existence so far, nor the lives of the younger men I’ve dated since college. How exotic.

That’s not to say my older dates were particularly high-rollers, yet compared to my fellow 20-somethings and I, they were rich (or so I perceived) in peace of mind. We could go all night without having the “I don’t know what I’m doing with my life!” conversation, which freed us up to discuss so many other topics. When we did get around to career talk, there was no silent sense of comparison or competition — they’d already cleared the early professional hurdles and assured me I would too. The stability was addicting.

But as I racked up my 0 for 3 record, I began to imagine that, again, like visiting another country, these older men came with customs I didn’t understand, rules I was oblivious to. Was I that drunk tourist trying to light a candle in Notre Dame Cathedral? Why did my visa keep getting revoked?

With each guy’s gradual disappearance, I tried harder to understand the foreign topography, feeling more misused and self-pitying with each question: Did my age automatically preclude me from a steady fling or (god forbid) a meaningful relationship? Was that the point? Is dating a 20-something the easiest thing a 30-something eschewing commitment can do? Just what did they see in me, anyway?

Maybe these are questions to which I won’t have the answer until I reach that age myself. If I had to venture a guess, however, I’d say it all comes back to the travel metaphor: I was as much a reality vacation for the 30-something set as they were for me.

After all, I was completely guilty of projecting a sense of security onto their lives that couldn’t possibly be real —it’s hard to believe anyone has “peace of mind” at any age. I’d found their company so enticing precisely because it was a break from my 20-something life and psychology. Why wouldn’t this work both ways? During the last conversation I had with one of my older dates, he mentioned he’d recently quit his job. Maybe he needed to quit our little vacation too, and return to reality and someone he felt could better understand his 30-something issues.

I’m not suggesting that like should date like uniformly. But I've personally vowed to date closer to my own age in the future. Splitting PBRs at the local dive bar ain’t glamorous, and pondering someone’s employment problems on top of your own sucks. At the same time, home is where the heart is.