He's 25 years younger and lives in another country

Monday | March 2, 2026

Love Letters Dating

He’s 25 years younger and lives in another country

Is there something on your mind about a relationship in your life? Or a relationship you wish you had in your life? Send your own question. Help others wondering the same thing. Use the form – or email [email protected].

My question is this: I know an incredibly sweet man who lives overseas in a tiny country. There is quite an age difference – I am 25 years older than him. He is very handsome, of course, and surprisingly single. I THINK. This has yet to be independently verified.

My question is: having had a long string of overseas boyfriends (I am an inveterate globetrotter), I know that they of course eventually go the way of the dodo bird. Yeah, as in extinct.

I now find myself in the exact same position again. I am trying to hold back for my own protection, if nothing else. I certainly have been down this roads a couple of million times.

My question is … is there a way to NOT make the same mistakes again? I know it never works unless one moves to the other’s country.

I could never leave Boston, at least not permanently.

– Globetrotter

You globetrot. How lovely.

But you like being home, too. You don’t want to move out of Boston. That means you should be dating in Boston – or New England, at the very least.

Let this be the second time in a month that I tell someone to expand their dating app geography to include Maine. It’s pretty up there.

There are more productive things to do with your time than pursue a maybe-single man who is 25 years younger and in another country. I’m all for flirtations that turn into life experiences and fun stories during a dinner party, but you say you’ve done this many times (a million). You already have these tales, and you know they come with hurt feelings.

Learn from your history and ask yourself, “Why am I seeking people who are so far out of reach?” Isn’t it time for a new kind of adventure?

Stop communicating with this faraway friend. Maybe join some local travel groups instead. You might meet someone around Boston who shares your drive to see the world.

– Meredith

Readers? What makes a person seek out partners who can’t be near them? What questions should the LW ask of herself?

Is there something on your mind about a relationship in your life? Or a relationship you wish you had in your life? Send your own question. Help others wondering the same thing. Use the form – or email [email protected].

Dating Distance

Featured Comment

You choose not to do the same behaviors. You allow yourself to feel the discomfort that arises without trying to fix it or calm it. And then you get some therapy to identify why you make those choices in the past. And every time the opportunity arises to repeat your pattern, you make a different choice and break your own pattern.

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