It depends. Do you have a problem with a May-December romance or do you think other people have a problem with it?

Share story

Dear Carolyn

Adapted from a recent online discussion.

DEAR CAROLYN: I’ve recently started chatting online with a considerably older man — closer to my parents’ age than mine. I swiped right because I thought he was attractive, but I didn’t really expect to ever meet up with him. A few weeks and many deep conversations later and I realized I feel a real connection with him and, as odd as it sounds, I can see a potential future for us. We’ve already talked about what that may look like … he even brought up kids and we are on the same page.

It’s way too early to know whether this will really go somewhere, but, despite our strong connection, the age gap has me wondering if I should end this before I get any more invested.

— Dating Older

DEAR DATING OLDER: If you have a problem with it, then it would make sense to end it before you get more involved.

If you think other people have a problem with it, then it would make sense to ask yourself why you would change the course of your life to conform to other people’s expectations. Even your parents’, if that’s what you’re worried about.

There are challenges to consider, of course. Think of every life stage you might have ahead of you, and then imagine having to navigate its challenges plus the challenges of an age difference and all that potentially entails.

Which isn’t to say it’s the main thing to worry about. The challenge of having to navigate life with a person you don’t love completely? That sounds hardest of all.

Like anything else, deciding how to deal with a big age difference is a matter of trade-offs, and of possibility versus certainty. Some people, for example, don’t worry about the possibility they will end up caring for and long outliving a much-older mate, because they choose the certainty of loving a cherished person in the moment, for all moments they can get.

If you can’t figure these things out with any confidence yet, then that’s fine, too. It’s OK to date someone now with the intent of learning as you go. That’s what dating is for. The pre-emptive breakup is for when you’re sure someone or something isn’t for you.

To: “Dating Older”: My husband is 19 years older than I am and we met after having both spent considerable time living independent lives. We knew what we had found with each other was special and profound. I am 47 and was recently diagnosed with a rare, extremely aggressive cancer. It is very, very unlikely I will outlive him.

While it can be easy to assume how life might go, and that the younger partner will be the caretaker of the older, real life could have no bearing on that assumption. Choose who you want beside you as you walk down any path and season of life, whatever may come.

— Anonymous

DEAR ANONYMOUS: Hear, hear, and take care — I hope you beat your odds.