By Mandi Bierly
April 30, 2012 at 05:16 PM EDT
Everett Collection

The thing about the fairy tales we’re told and the Disney movies we watch as children is that while they may start off with a tragedy, there’s always a happy ending. Over the weekend, the 1991 movie The Man in the Moon was on cable, and I was reminded how much it scarred me as a teen. If you don’t remember it, Reese Witherspoon stars as a 14-year-old who replaces her crush on Elvis with a crush on the teen farmer next door, Court (Jason London). Just as he finally accepts their age difference, he meets her older sister and falls for her. Then, distracted by postcoital bliss, he falls off a tractor while reaching for his hat on a tree limb AND DIES. Clearly, I had not seen the trailer for the movie, which gives that away. I was devastated. It hurt my soul…each and every time my sister and I watched it on HBO because we, too, had a crush on Jason London. 

Thinking back to the entertainment that truly taught me about heartbreak, two other memories are even more vivid: The first was when I watched a repeat of Brian’s Song on TV. I think I was a tween, because I remember being too big to really fit on my mother’s lap, which is where I sat sobbing uncontrollably. She’d told me not to watch it, but I did anyway. I can still picture myself running to her chair in the living room and wrapping my arms around her neck and wailing. The other memory came flooding back recently when Dick Clark passed away. My mother used to have a best of American Bandstand VHS tape that included Mark Dinning performing the song “Teen Angel.” I can’t count how many times I replayed it — him sitting on that stool in the spotlight, me just trying to process why the girl he was singing about would have gone back to the car, which had stalled on the railroad tracks, to retrieve his high school ring, which they found clutched in her fingers tight. I think a part of me was hoping I misunderstood the song, or that if I listened to it enough, the ending would eventually change.

Your turn. What entertainment introduced you to true heartbreak as you were coming of age?

Read more:

25 Best Tearjerkers ever

PopWatch Confessional: Name the movie you want to watch again but can’t bear to because one moment is THAT sad

PopWatch Confessional: When you need a good cry, what is your go-to movie scene?