The Truth About Dating Older And Younger Men

At 59 and divorced after 25 years of marriage, I feel I’ve earned a few luxuries: comfortable shoes, the right to leave parties early without inventing a fake headache, the ability to lie on my couch all day binging whatever show I want, and the freedom to date whomever I please. I’ve lived long enough to know that life is short, my time is precious, and my nonsense era has ended.

So, the question is no longer whether I can date, but where I should aim my romantic compass: toward older men or younger ones? Both options come with their own peculiar mix of promise, peril, and the occasional urge to fake my own death.

Dating older men feels a bit like slipping into a well‑worn cashmere sweater. It’s soft, familiar, and there’s a very good chance it already knows how to behave in public. Older men tend to pay for the date and open doors — two things I consider the height of modern romance. If you want to win my heart, start with the check and the car door please.

There’s also something comforting about being with someone who understands the importance of a good night’s sleep. An older man has lived long enough to know that communication isn’t optional, and occasionally he even knows how to apologize — though I’ve learned not to get too excited about that too early. Hope springs eternal, but so does denial.

But there are downsides. Conversations about retirement have a way of drifting into conversations about health, and that’s not exactly what I’m looking for when I put on lipstick and heels. I don’t want to talk about retirement homes yet. I want someone who is still working, earning money. To spend on me. Is that so wrong?

Then there are younger men, who feel less like a cashmere sweater and more like a leather jacket I’m not entirely sure I can pull off—but I try anyway, because why not? If not now, when?

Younger men bring energy into the room, and not the kind that requires a nap afterward. They are curious, engaged, and often genuinely intrigued by me, which is both flattering and slightly suspicious. There’s something thrilling about being chosen by someone whose dating pool includes women named Skylar, and yet here he is, having dinner with me, a woman who remembers when phones had cords and dial up internet.

And yes, there’s a rebellious part of me that enjoys defying expectations. People are perfectly comfortable when older men date younger women but reverse the roles and suddenly everyone becomes very interested in my life choices. I can’t pretend I don’t enjoy that just a little. It’s like being cast in a scandal no one asked me to audition for.