My high-school ex is an embezzler

Should I write to him in prison? Should I send him money for toiletries?

Published June 10, 2013 12:00AM (EDT)

                                                                                                                                                                                                                                                                                                                                                                                                                       (Zach Trenholm/Salon)
(Zach Trenholm/Salon)

Dear Cary,

An old boyfriend from high school has ended up in jail for embezzling funds through his law practice. I was browsing through Facebook and found a news link that explained his circumstances.

We are in our mid 60s. I am happily married and not looking for a hookup. Is it a good idea to write to him? He is in a medium security prison for four years. The conditions are likely not good. Apparently, you have to buy your own toiletries, food treats, etc.

When I initially read of his being convicted and losing his practice, I was appalled and since I had good memories of him, I still believe he is a good person at heart who made some really bad decisions. Would it be helpful to him to hear from someone who remembers him the way he was? Or should I just ignore the fact that I know what is happening to him?

I have looked other former friends up online, mostly out of curiosity. A few I contact, most I don't bother. What do you think?


Dear Curious,

I suggest you talk this over with your husband if you haven't already. Not that you need his permission. But you should talk about it. Your desire to help puts you in a vulnerable position.

Also, if you haven't yet, ask yourself why. Is a fantasy brewing below your level of conscious awareness? Are certain sweet memories percolating? Is part of you wishing for a reenactment of high school's hot, sweet crush?

Of course if it's happening unconsciously, you don't even know it's happening. That's what con men prey on. They use our own unconscious impulses to manipulate us. If they can get us to to step over the line in some way, then they have an advantage. So if you were thinking of writing to him secretly, don't. Talk it over with your husband. And if you find you are resisting that, ask yourself why. Otherwise, you are in danger of doing just what your ex-boyfriend did: making a "bad decision."

There's nothing wrong with corresponding with him openly. But if you do it without telling your husband, it would be like emotional embezzlement.

So if you can do something to make his life easier and if that makes you feel good, go ahead.

Just don't help him out secretly. Talk it over.

By Cary Tennis

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