“Like most long-term friends, we knew a lot of each other’s secrets. Misdeeds, misadventures, and so forth. Nothing too criminal but also some youthful indiscretions that should stay in the ‘we don’t talk about this with others’ box.”
“The friendship was waning. About a year prior, I had started questioning what I was getting out of it and if I should or shouldn’t slowly break contact. Then I started dating my girlfriend. Naturally, my friend took that as me dropping him like a hot potato, which wasn’t true, but from his perspective, I get the suspicion.
After a few half-hearted attempts at getting together, we did, and apparently, he did not like the way it turned out. He sent me an e-mail threatening to tell my girlfriend all of the shit we’d got into over the years, going so far as to list out dates, times, and circumstances. I responded that he could if he wanted to, and that would likely be the end of the relationship with my girlfriend, but the threat of doing so definitely meant an end to our friendship. I also forwarded the e-mail to a couple of friends who were already in the know. They also ended up cooling things off with him.
In the end, nothing came of it. But when you start threatening your friends of 20+ years with misdemeanors committed when you were young, then I can never trust you again.”