Rank your favorite romantic pairings from the iconic Upper East Side drama! From the legendary on-again, off-again relationship of Blair and Chuck to the complicated love triangle involving Serena, Dan, and Nate, Gossip Girl delivered some of television's most memorable couples. Whether you're team Chair, team Derena, or rooting for the underdog romances, this ranking lets you organize all the show's relationships from endgame-worthy to totally toxic. Evaluate the chemistry, drama, and ultimate compatibility of each pairing as you decide which couples deserved their happy endings and which should have ended before they began. XOXO, it's time to spill the tea on Manhattan's most elite relationships!