Anonymous wrote:This summer my mom gave me a box of letters and other mementos from middle and high school that had been in their attic for years. It was amazing how many letters I was clearly exchanging with friends - when we travelled for summers away, people I met at camp, friends who had done study abroad, etc. In college I got an email account (this was the mid-1990s so no one I knew had internet at home yet). It really made me nostalgic for the lost art of letter writing.
To answer OPs question, I read through some of the letters from past boyfriends, cringed heavily, and recycled. I did keep a some photos from prom, etc.
My mother threw them out without asking me. My husband (not the boyfriend) was furious, because he went through early losses of family members and values these kind of mementos for anyone.