TV’s Saddest Breakups (PHOTOS)

They totally do it on the Season 6 Premiere, but is it a flashback? There’s no denying Chuck and Blair have INSANE chemistry, and there are no two people better equipped to scheme symbiotically than these privileged punsters. Plus, their shopping moments must be EPIC. But will all the lying, scheming, and timing issues ever give way to happiness that is everlasting (and not boring)? We only have 10 more episodes to find out...