Can she be cautious with an old flame who was a cheater?

Dear Carolyn: I’ve been single for over 20 years! Recently an old boyfriend from many years ago contacted me and our longdistance conversations have been delightful. I’m intrigued by this unexpected new possibility.

I also feel extremely cautious. Our past relationship ended because he cheated. He has now revealed he had an affair as his marriage was falling apart, and he continued that affair for some time, despite being “friends” with the woman’s husband. He also says that affair ended several years ago.

I know I’m right to be cautious, given this pattern. And yet there is a spark with this old flame that I’m really enjoying. How do I proceed? — Intrigued but

Cautious

Intrigued but

Cautious: The shortest distance between those two points is to assume he’ll do it again, to you.

No guessing, no fretting, no wondering what he’s up to. Expect he’ll have someone(s) else.

Can you enjoy companionship for the sake of it, without promise of commitment or exclusivity?

I actually think you’re wrong to be cautious. “Cautious” implies something can be done safely.

Some things are dangerous. Like mountainclimbing. You don’t tiptoe up, hoping the mountain has changed. You go into it knowing what you can and can’t control, equipped to handle the worst — because the mountain is calling your name.

Or does this romanticize jerks? Maybe it’s more like riding without a helmet.

Anyway. If you’re not equipped for danger, then stick to lounging poolside.

Dear Carolyn: Because of a lifelong mismanagement of finances coupled with some misfortune, my partner and I are in the position of needing to support his parents. After covering a car payment, cellphones, utilities and other bills, we also give them a sizable sum each month for living expenses. We can afford it but not easily, and it does mean we sacrifice in other areas, like our kids’ college funds, our own retirement, etc.

We just found out they donate half of this sum each month to their church. We were floored.

In addition to not supporting their church of choice — they openly discriminate against LGBTQ people, when our child identifies as one — we are upset the money isn’t being used for what we intended.

Should I assume once the money goes to them, we should butt out?

— Floored

Floored: Oh yeah no. There is a really great ethical conversation to be had here, which I’d join just as soon as I stopped supporting people who support a cause that hurts my child.

Talk to your partner about paying specific bills vs. handing over a block grant, and restoring as much as you can of your retirement. Don’t fix their mistake by repeating it.