Jessica Szohr and Ed Westwick, 2008–09
While Penn Badgley and Blake Lively hold the crown for most-loved couple on the Upper East Side both on and off-screen, Szohr and Westwick took a stab at romance, too. “It kind of just happened. We had fun together, and we were like, ‘All right, let’s see where this goes,” she toldTeen Vogue in 2009. The couple reportedly dated on and off until 2012, the same year Gossip Girl ended.