Carolyn Hax: A cheater can’t change his spots, so assume he’s still fast company

By Carolyn Hax,

Dear Carolyn: After a string of failed relationships I shifted gears and started working on myself. I’m pretty happy with my life now, but I’ve been single for over 20 years!

Recently an old boyfriend from many years ago contacted me and our long-distance 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 with a heart open to new possibilities while still protecting myself from his old patterns?

— 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. Conduct your relationship accordingly.

Now ask yourself: Can you do that? Can you enjoy companionship for the sake of it, without promise of commitment or exclusivity or, in his case, any hope he’ll change?

Can you open your heart because you trust yourself with it, and any consequences? Can you enjoy love for the experience and not fear the hurt?

Can you see yourself inviting him into this kind of honesty, where you tell him you will enjoy his company but will not tie yourself down to someone who doesn’t hold fidelity in the same regard you do? Because you have a great life now on your own terms and won’t trade down?

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

Some things are dangerous. Like mountain-climbing. 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. No shame in that. The value in any choice is not absolute; it’s in how well you know yourself, and how well your choices suit you.

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.

I don’t want them to feel like they have no control over their lives, but I also don’t want to be spending thousands of dollars a year on an organization we don’t support when it could be put to better use to support them or our family.

Am I right here? Or should I assume once the money goes to them, we should butt out and let them decide?

— 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.

You, of course, are free to think differently, empower the recipients fully, give as always. No judgment. Yay, America.

There is so much gray, you’re right, in how a recipient spends money given by others. The purpose of the giving matters — gift money is string-free but this is toward solvency, which to me is different. And the nature of their insolvency matters. And what they spend it on matters.

To donate to a cause that undermines their own grandchild — using said grandchild’s tuition money! — is both a gobsmacker and hardly surprising, these days, and to my mind it’s enough of an outrage to matter.

Your in-laws’ autonomy deserves a nod as well, even though they squandered much of it themselves.

I could also argue the ethics are a luxury neither of us can afford here: For my purposes they’re beside the point, and you literally can’t afford them. Your in-laws can spare this money, so your retirement and college funds don’t have to. Done.

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

Write to Carolyn Hax at tellme@washpost.com. Get her column delivered to your inbox each morning at wapo.st/haxpost.