they would have dated for a little over a year (early 2002 to summer 2003) and it ended when he basically left town out of the blue with his band after he graduated. she either graduated the same year or the year before and had decided to stay in boston in part because she thought he would be there - he never had plans to go to college - so him leaving was quite a shock and she held animosity towards him because of it for years. i had in mind that she was more popular than him (that can be in the nice girl way or hbic kind of way) and they snuck around for a little while before people caught on and then they didn't care. ryan was mainly known as a guy you could go to for weed and who might have other favors at parties on occasion, plus the guy that would occasionally fight bullies if they fucked with people he was close to.