Dear Reverend,
More than 20 years ago, my childhood friend and I dated. He always had a crush on me, and I liked him, too, so once we were in our twenties we decided to give it a try. Things didn’t work out, and I have not seen or heard from him since. My sister ran into him at an event, and they talked briefly. He has been married and divorced two times, and I discovered he only lives 15 minutes from me. With that said, it brought back a lot of memories and past hurt. I mourned the loss of our friendship and was hurt when he chose to disconnect from me and everyone close to me. Do you think it’s a good idea to reach out to him?
Cold Shouldered
(woman, 45)
Dear Cold Shouldered,
If a long-lost friend randomly pops into your head, I usually believe you should reach out to them, but this situation isn’t quite like that. The best way to answer your question is to ask yourself a few.
Have you thought about getting in touch with this fella over the past two decades? Or is he only on your mind because your sister mentioned him and it stirred up old, bad memories? If the latter, you ought to let the idea go. The past may best be kept in the history books.
If you have occasionally found yourself pining for your pre-dating friendship, though, go for it. Your sister bumping into this guy gives you a good reason to get in touch, but the million-dollar question is: What do you want to say to him?
If you feel the need to rehash the bad memories, I suggest that you get it all out in a letter. (A phone call might be too much of a surprise.) Sit on what you wrote for a day or two, then reread it and throw it in the trash. That exercise may be enough to get it out of your system and be done with it.
However, if you truly want to extend an olive branch of friendship, keep the note short and simple. Let him know you were thinking of him, wish him well and give him a way to get in touch with you if he’d like to. The ball will be in his court. If he volleys it back, you can take it from there.
Good luck and God bless,
The Reverend
This article appears in August 12 • 2026.
