Milwaukee Journal Sentinel

Should she be cautious with cheating old flame?

- Carolyn Hax yourself – Floored Email Carolyn at

Ask Carolyn

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 affair as his marriage was falling apart, and he continued that affair for some time, despite being “friends” with the woman’s husband. He also says that affair ended several years ago.

I know I’m right to be cautious, given this pattern. And yet there is a spark with this old flame 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 with it, and any consequenc­es? Can you enjoy love for the experience and not fear the hurt?

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 finances 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 afford it but not easily, and it does mean we sacrifice 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 floored.

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

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

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.

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.

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

tellme@washpost.com.

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