Dear Carolyn: After 30 years, an old high school “girlfriend” (mostly hookups) has contacted me expressing her regret that we never “had that opportunity to further our relationship.” We have emailed for a month now, and I find her smart, funny and interesting, but I have a concern: She is three times divorced.

Is it possible that her repeated failures in that department were not her fault, as she says? Her exes were substance abusers and adulterous, by her claims.

I am wary of getting involved. Am I being too judgmental? Should I be open to the idea that she just had bad luck? By the way — I am divorced once and, at 50, do not want to waste my time on someone who is unstable. Would you get involved someone with three exes?

Re-connections

I won’t say yea or nay to getting involved with someone thrice divorced, since circumstances, timing and lessons learned are too personal to judge collectively — but I sure would want to know the stories. For example, one youthful oops marriage, one marriage to someone who became an addict, one marriage that lasted decades until the spouse had an affair or something … well, running away would almost seem punitive of someone who gave a good-faith effort to get it right.

If instead each divorce had a similar story behind it, then I wouldn’t stick around unless I felt darn sure the person had had the “Eureka!” moment and done the hard work of breaking unhealthy habits — starting with accepting responsibility for making bad choices.

Since you’re talking about someone who apparently married the same general pathology three times, and who is blaming the exes for that versus noting the pattern in her own choices, and who is fishing in the electronic waters of 30 years ago, I’d urge you to write your next email without the input of any organ south of your brain.

Dear Carolyn: Ugh, ugh, ugh. I sent a message to a friend I haven’t seen for a while this week to see if she wanted to get together soon, and she said in her response that her husband now has his own apartment. They have two young kids, and this comes seemingly out of the blue. Our husbands have been friends since junior high, and I’ve known them for about four years.

We’re getting together with our kids next week, and I’ll presumably get more of the story then, but I’m totally at a loss as to what to say or do. These are our first friends to get divorced and, to make things worse, this is her second marriage, so I’m worried about any fallout from that, too. (The first time she was very young and the guy turned out to be abusive.) Any advice?

Friend

The best, best, best thing you can do is not bring an agenda with you. Not pro-reconciliation, not pro-husband or pro-her, not anti-multiple-divorce, not pro-divorce-is-the-end-of-the-world.

If you need an agenda to orient you, make it pro-friendship. Listen, don’t judge, and see what she needs based on what you see.