Should you take chances on an ‘ex-’ cheater?

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

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November 11, 2020 - 9:08 AM

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.

Carolyn HaxCourtesy photo

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 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? 

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.

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.

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