Buffy the Vampire Slayer: Buffy vs. Angelus
Season 2, Episode 22: Buffy’s second season saw a noticeable uptick in fight-scene quality, but it’s the emotional underpinning here that’s really a sword to the gut. After spending the last several episodes coping with her boyfriend’s return to his murderous, soulless vampire ways and trying to restore said soul, Buffy realizes she not only has to fight Angelus (as Angel calls himself now), but kill him and send him to Hell. And just as Buffy’s sword goes through his heart, Angel’s soul comes back. Breakups don’t really get any worse than that.