Maybe you lost someone you never expected to lose. Perhaps you lost yourself, that's even worse. Crossing paths with Dean Winchester was never in Leah Cartwright's plans, but some things seem too real to be mere coincidences.
Imagine meeting Dean Winchester back in highschool and things get so complicated you have to part ways with him, only to meet him again later in your life.
"If you love someone, you should always go after them" people often say but I think if you are lucky enough for fate to care about you, life will always find a way to put you back together.