What was your most painful break up like/over/how old were you, etc??

The one guy throughout high school. Maybe it was just a high school thing and wouldn’t have lasted, but we were most definitely in love at the time. But after we graduated, his family decided to move far away, for whatever reason. We didn’t break up by choice, so that just made it all the more heartbreaking. Sure, I’ve since moved on and am now married, but I still miss him. If he were around, I would love to still be friends.