Carolyn Hax: When to tell a friend you used to date her new boyfriend

Hello, Carolyn: One of my best girlfriends (we’re in our 40s and 50s) has started dating a former lover of mine. Because I’m a private person, my friends possibly knew of him – I’m single – but didn’t press for details. They all know him independently through a group affiliation we share.

He became “former” earlier this year because he constantly let me down, from canceling a date as I’m literally on my way, to taking a phone call while I’m talking with him about facing my oncologist about my cancer progress – the whole range of disrespectful. No biggie, I respected him enough to accept how he wanted to be, and we just transitioned back to friendship.

A few weeks into their dating experience, however, he’s already doing the same to her – last minute cancellations, etc. Her desire for marriage may blind her to how disrespectful his behavior can be.

So, two questions: Do I have to crack my own shell of privacy and tell my friend I had a thing with a guy she’s now dating? He’s obviously not mentioned it. If I wait to see if it becomes serious, then it’s an even harder conversation. I feel really uncomfortable about each of the say/don’t-say options.

And do I share with her some of the thoughtless and disrespectful things he’s done? Not least of which, I think, is dating one of my best friends without a heads-up to me.

Maybe I should talk to him? I don’t like being in this position! – Say/Not Say?

These lose-lose decisions always feel the hardest, obviously, because you don’t see any courses of action you like but inaction leaves you stuck in the limbo of facing an unwanted choice. It’s lose-lose-lose, in a way.

But there’s usually a good decision – or a merely less-bad one – to be found by breaking a situation down to its most basic facts.

Here, you have two certainties at the foundation of everything: Your privacy is yours, and your friend’s relationship is hers.

So your best choice is going to be the one that comes closest to honoring these two facts.

Which means you say as little as possible, and you disrupt the relationship as little as possible.

You rightly point out that choosing to say nothing will loom larger and get weirder as their relationship progresses. That means speaking up might feel like butting into their business but is actually more respectful of their relationship – and your privacy – than silence. Silence plants a drama mine that one of you is almost certain to step on someday.

The truth gains potency daily, so speak up soon. “I should have said something right away, I’m sorry – I erred on the side of minding my own business but instead it felt like keeping a secret from you. Anyway, I dated [name] for [time period], until [date]. That’s all. I’m happy for you both.” Crack your privacy now, on your terms, to pre-empt its demolition by others later.

“That’s all,” by the way, means no comment on his thoughtlessness (or her marital-desperation blindness, ahem) because their actions and feelings and relationship are theirs. Yours become relevant only when you’re asked, and even then, you speak only of and for yourself.