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I would like to get to know a kind man who was an officer where I was incarcerated. Is there a chance?

After being released, I thought of reaching out to him.

Love Letters

Need relationship advice? Submit your questions for Meredith here.

Q. Is it right or wrong to tell someone you have feelings for them?

We don’t know each other, other than the fact we randomly see each other. I, a woman, decided to take a leap of faith and let this person, a man, know I have romantic feelings for him. I used an anonymous letter mailing service to do this.

This man has wonderful energy. I am not labeling him perfect, rather someone I would like to get to know to see where things go. He is a high-ranking officer where I was incarcerated. I made some bad decisions with the wrong people, which then led to me being incarcerated (white-collar crime). After being released, I thought of reaching out to him. Having romantic relationships there is not allowed, and I am not in the business of jeopardizing someone’s career over an attraction.

Not sure what may happen after this letter — if anything. I arrived at the conclusion that I will never know unless I try. Is it worse being turned down and feeling humiliation, or not knowing? Thoughts on this?


– Anonymous

A. Speaking generally, there’s nothing wrong with telling someone you have feelings for them. As for humiliation vs. not knowing . . . is it really humiliation? Rejection is part of life. Usually, after a few days, it feels less intense, and it’s not the end of the world.

But about these disclosures: If you meet a crush at work, or in a place where romance isn’t allowed (your situation), it’s a different thing. There are rules to consider. You don’t want to cause someone discomfort on the job.

The question is whether your disclosure is OK now. All I can say is that if and when he answers this letter, listen to what he says. If he doesn’t respond or replies that he’s not interested, end it there. That’s the big thing — to respect the other person’s wishes and boundaries. Also know that it might be frowned upon, in his profession, to date people he met at work, even after they’ve moved on.


As for the anonymous mailing service, I am concerned. Did you use it because you know he wouldn’t want to open a letter sent by you? Or because his colleagues would flag the content based on you being the sender? You’ve already made your decision, but consider that it might be better to pursue a relationship that doesn’t involve having to hide.

This is a great time to talk to a therapist about how to form bonds in this new chapter of life. This man might have great energy, but he’s not the only one.

— Meredith


There are 4-plus billion other dudes in the world. I suggest you take an interest in a different one. GDCATCH

If you went so far as to use an anonymous service to share your feelings, odds are you’ve gone too far. You aren’t wrong to share your feelings, but professional boundaries are in place for darn good reasons . . . Let this go. PENSEUSE

I can neither confirm nor deny that I work in this “industry.” If I did, I would say that most “employers” prohibit staff from dating former “customers,” regardless of circumstance. WARMACHINE


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