6. Season 5: Bye Bye Riley
I know a lot of people really didn't care for Riley as a character... but I am not a lot of people, and actually think Riley was exactly what Buffy needed in her life at that time, and perhaps was the perfect guy for Buffy in the long term. If we are admitting to liking unpopular characters, I will also admit that I love Dawn... in fact her character easily became one of my all time favorites on the show by its end. Anyway, the season 5 episode "Into The Woods" is one of my all time favorite episodes of Buffy The Vampire Slayer and shows Buffy having to make a tough decision as to whether or not to decide to stay with Riley, or allow him to leave town and risk never seeing him again. Buffy struggles with the decision, especially seeing as Riley has been secretly allowing himself to be bitten by vampires for the rush of it for weeks now. The whole episode is really devoted to watching Buffy go through this potentially life changing transition, and any episode directly focusing on Buffy's inner turmoil is fascinating to watch. In the end Buffy decides to forgive Riley after a heartbreaking monologue by Xander (one of many) where Buffy realizes that she is at least in part to blame for their relationship troubles. She runs through the woods to try to stop Riley from leaving town on a helicopter, but although Riley waits for a while, hoping Buffy will return to him, Buffy is just too late, and Riley will never know how Buffy truly felt. Fortunately it all works out well for Riley in the end, and his leaving probably worked out quite nicely for most of the audience who hated him as well.