Jessica Szohr and Ed Westwick ("Gossip Girl")
When Chuck hooked up with Vanessa on "GG," it was pretty shocking. But in real life, there's nothing shocking about a drop-dead gorgeous actress dating her handsome British costar. Alas, the two broke up in April amidst cheating rumors.
Blake Lively and Penn Badgley ("Gossip Girl")
Blake and Penn are the Upper East Side's oldest and longest-lasting couple, even outlasting their characters' relationship on the show. These two crazy kids started dating after meeting on set, and have been together since late 2007.
Leighton Meester and Sebastian Stan ("Gossip Girl")
Despite the occasional paparazzi shot, Leighton and our former Hump Day Hottie, Sebastian , did an excellent job of keeping their romance out of the tabloids. That is until they broke up in April, when the split made headlines all over the place.