My guy friend winked at me after saying a bunch of people including me were the loves of his life (jokingly), tried to hug me in a joking manner, and always teased me. On the last day of school he seemed pretty sad. Did he like me?

He was probably dropping hints that he likes you a lot and wants to keep in contact over the holidays, chatting with him and meeting him would maybe keep a smile on his face, and if your the reason to that smile then yeah he has a crush! If theres another reason then don't rush the friendship to a higher level, bad Idea :) hope this helped