I sat in a hardwood Eames chair in a friend’s kitchen, listening to the slow unraveling of her relationship with a man in his 30s. True to her words, he didn’t seem to care much about her; During a recent row, he admitted his feelings can’t be hidden – which is a crazy thing to say to someone he’s dating. Ultimately, it’s clear that what once seemed like “tough times” won’t be over anytime soon.
My friends and I have been here many times before. While the details have changed, the story is more or less the same: a small slight, then a bigger slight, then an unsettling silence, followed by some brief reconciliation that erases nothing. It became almost a ritual—listening to her account of events and then making some mild suggestions that she wouldn’t accept, both of us vaguely aware that we were participating in something pointless.
However, after a few months, my sympathy waned. As I watched her from across the kitchen table, waiting to say my lines, I found that I suddenly had no interest in repeating myself.
So I changed my strategy. “Maybe,” I said after a long pause, “it’s time to try dating someone older than you are.”
My own boyfriend is more than twice my age, which is either shocking or impressive, depending on who you ask. This was my first date with a much older guy and I would sometimes joke with my friends that I was missing out my whole life.
There’s something to be said for a man who’s had more time to sort out his own affairs, and my much older boyfriend seems genuinely happy to be with me – not like he’s biding his time to find someone better. He’s fully aware that he’s a lucky bastard.
We met at a birthday party. I sat down next to him at a long table and started talking, as I often did when no one was supervising me. I just returned from a solo trip to Hawaii and rented a small cabin on the beach in a town most people have never heard of. It turned out he had owned a house there for over 20 years. This was the place I would return to for the better part of a decade, and he was always there, just down the road. We joke about whether we’ve ever passed each other on the same beach or stood side by side in line at the same health food store. As we continued talking, we soon realized that our lives intersected in other ways too, an invisible rope connecting us.
The age gap went unnoticed at first. I met an interesting and charming guy; if anything, I thought we were just going to be friends. But when we exchanged phone numbers and made plans to go get coffee, I called my best friend, the only guy I knew who was dating older than me.
“Should I go on this date?” I asked.
“How old are you?”
“Over sixty years old.”
There was a pause, then: “Oh my God. He’s a chick.”
***
I’ve noticed how differently people react to age gap relationships depending on who occupies which side of the gap. Take Cher, for example, who is dating someone decades younger than her. Generally speaking, the response is: Good for her. one Pop icon, 79, wins the right to enjoy life. The opposite arrangement produced a different type of comment. Older men are instinctively labeled as “creepy” and “disgusting,” while women “must have daddy issues” or must be a money digger. Is it really so hard to imagine that two people of different ages could find something real in each other, across generations?

