#33: Blake Lively and Penn Badgley

Duration of Relationship: 3 years (2007–2010)

The 2010 breakup between Blake Lively and Penn Badgley was bittersweet for Gossip Girl fans, who had rooted for their on-screen and off-screen romance. Having dated for three years while starring on the hit show, their relationship seemed to mirror their characters’ passionate connection.

However, as they grew older, the two drifted apart, citing different life paths for their split. Despite the breakup, Lively and Badgley maintained a professional and friendly relationship, continuing to work closely on Gossip Girl without any public drama.