Dear Cary,
For a few years now, I have had very strong feelings for a friend of mine. He and I are not close friends but occasionally spend some time together. He is the brother of a very close friend, and I have liked him for about three years.
I have liked and dated other men. But the brief relationships never got off the ground, and I always came back to C. I have always felt that there is something between us, but he is never going to do anything about it. He has never dated any women, and he is not gay.
A mutual friend who wants C and me to date has shared some of C's history with me. His father had a torrid and public affair with the wife of his best friend while C was in high school. The parents stayed together but never talked about it. I am not even sure the younger family members even know this ever happened. And the only girl anyone ever knew he liked slept with his best friend about 10 years ago and he has never been the same since that night. It is as if he has shut down completely.
I know his family very well, and I am in love with him as much as I can be without someone reciprocating the feelings and affection. The problem I need help with is how to talk to him about it, and what to say. I have a terrible history with men, and a crippling fear of rejection. But I know that this will continue unless one of us says something, and I am the one who has to get on with life.
Is it OK to put this all in a letter? No one writes letters anymore, and is that creepy? A blunt conversation may not be possible since I am not sure I can do this without any emotion.
Ready to Move On
Dear Ready to Move On,
I think letters are great for such a situation. They're kind of old-fashioned, which makes them special. And you have the opportunity to spell out the nuances of your feelings. You can get the whole thing down. And you can revise. So I say yes, write him a letter and then send it to him in the mail, or just give it to him if that's more convenient or more private. Write it out longhand if you can. There's something about longhand writing that feels intimate.
Make sure in the letter that you provide some way for him to communicate back to you safely. If you want to meet with him after he reads the letter, then propose that in the letter. If you want him to write back to you or call you or e-mail you, tell him that. Whatever you choose, put some kind of date on it, so you know that if you don't hear back by a certain time, it means he's not going to respond favorably. That way you won't be wondering forever, and it will give him some kind of out, and no matter what happens, you can move on with your life.
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