I was sitting in my friend’s kitchen, on one of those hard wooden Eames chairs, hearing about the slow unspooling of her relationship with a man in his mid-30s. As she told it, he didn’t seem to give much of a fuck about her; in a recent argument, he’d admitted that couldn’t fake his feelings—a wild thing to say to someone you’re dating. Ultimately, what had once seemed like a “rough patch” clearly wasn’t ending any time soon.

My friend and I had been here many times before. While the details changed, the story was more or less the same: a small slight, then a larger one, then a period of uneasy quiet, followed by some brief reconciliation that erased nothing. It had almost become a ritual—listening to her version of events and then offering a few gentle suggestions that she wouldn’t take, both of us dimly aware that we were participating in something pointless.

After a few months of this, however, my sympathy had worn thin. As I watched her from across the kitchen table, waiting to deliver my line, I found I suddenly had very little interest in repeating myself.

So I changed my tack. “Maybe,” I said, after a long pause, “it’s time to try dating someone older.”

My own boyfriend is more than twice my age, which is either alarming or impressive, depending on who you ask. It’s my first time dating someone significantly older, and sometimes I joke with friends that I’ve been missing out my whole life.

There is something to be said for a man who’s simply had more time to get his shit together, and my much older boyfriend seems genuinely excited to be with me—not like he’s biding his time before he can swipe for someone better. He is fully aware that he’s one lucky bastard.

We met at a birthday party. I sat down next to him at a long table and started talking, as I tend to do when left unsupervised. I had just returned from a solo trip to Hawaii, where I’d rented a tiny cottage on the beach in a town so small most people have never heard of it. It turns out he has owned a house there for more than 20 years. It was a place I’d been returning to for the better part of a decade, and he had been there the whole time, just down the road. We joked about whether we’d ever passed each other on the same stretch of sand, or stood in line next to each other at the same health food store. As we kept talking, we quickly realized our lives had crossed in other ways too, an invisible string connecting us.

The age gap didn’t register at first. I had met someone interesting and magnetic; if anything, I assumed we’d just become friends. But when we exchanged numbers and made plans to get coffee, I called my best friend, the only person I knew who had dated much older.

“Should I go on this date?” I asked.
“How old?”
“In his 60s.”
A pause, then: “Oh my God. He’s a spring chicken.”

***

I’ve noticed how differently people respond to age-gap relationships based on who occupies which side of the gap. Take Cher, who is dating someone decades younger that she is. Broadly speaking, the reaction is: Good for her. A 79-year-old pop icon has earned the right to enjoy herself. The inverse arrangement produces a different kind of commentary. An older man is reflexively labeled “creepy” and “gross,” while the woman “must have daddy issues” or must be a gold-digger. Is it really so difficult to imagine that connection can exist across generations, and that two people of different ages can find something real in each other?