Double Dating in Our 50s: Grown-Up Giggles and Second Chances

I hadn’t seen my dear old friend Speedy (a nickname that’s stuck since college) in quite some time. We don’t live in the same town, and—like so many friendships—we let life get in the way. Kids, work, the usual “too busy” yada yada yada. But we reconnected at a college event, and there we were: two women in our 50s, each showing up with a boyfriend.

Yes, boyfriend. That word feels almost juvenile at our age, doesn’t it? But that’s what we’ve got. And honestly, it’s kind of perfect.

If you’ve read my other post, The Man I Became, you know I was single for a long time. Speedy, on the other hand, lost her husband many years ago—a heartbreak that reshaped her world. So here we are, both navigating the dating scene again, decades after we first learned how.

We introduced our partners to each other, and it was surprisingly delightful. So delightful, in fact, that we planned a double date. Picture it: four fifty-something adults, all learning how to date again. And for some reason, it struck me as comical. It felt like college all over again—giggling, flirting, and soaking up the fun. Except this time, we skipped the drama and the superfluous nonsense that tends to bog down the younger crowd.

We’ve met up a few times since, and each gathering gets better and better. There’s something magical about reconnecting with a lifelong friend and watching your new love get to know someone who knew you back when you were still figuring it all out.

Dating in your 50s is a curious mix of challenge and excitement. You’re set in your ways, sure—but you’re also at a stage where you can truly appreciate someone for who they are. No games. No masks. Just real connection.

So, here’s to me and Speedy—for putting ourselves out there, for embracing the silliness, and for finding a couple of great guys who are willing to laugh along with us. Because let’s be honest: we can be a handful.

Now it’s your turn. If you’ve dated in your 50s—after a breakup, a loss, or maybe for the first time ever—I’d love to hear your story. What surprised you? What made you laugh? What reminded you that love, at any age, is worth the risk?