1
Buffy and Angel: Buffy the Vampire Slayer
The break up made sense, a vampire and a slayer just couldn't stay together, but that just made it all the worse. Angel's blunt demeanor hits you like a lead pipe, leaving the audience bruised and distraught.
2
Sam and Diane: Cheers
The words "Get out" have never felt so cruel. Damn you Sam, damn you.
3
Carrie and Aidan: Sex in the City
Sure, Carrie was supposed to end up with Mr. Big, but I wanted to believe Aidan was going to win out in the end. He's just more interesting.
4
Winnie and Kevin: The Wonder Years
If this doesn't remind you of your first childhood crush, then I assume you've never had a childhood crush.
5
Cristina and Burke: Grey's Anatomy
Freedom has never looked so painful.
6
Holly and Michael: The Office
Sure Michael may be an idiot and this maybe completely awkward, but his pain is horribly real. You can't have comedy without tragedy.
7
Brittany and Santana: Glee
Just because it's logical, doesn't mean it still won't hurt like a bastard. Was it the right decision: probably. That doesn't make it suck less.
8
Cory and Topanga: Boy Meets World
Sure, maybe they do get back together. But this moment was the moment Cory finally grew up.
9
Joey and Pacey: Dawson's Creek
Damn Pacey, you cold. But, in his tantrum there is truth. Still shouldn't have done it on the dance floor though. Arguments, like sex, should be in a private room. Unless it's group sex, I suppose.