All of Dan Humphrey’s Girlfriends on ‘Gossip Girl’, Ranked

Dan Humphrey (Penn Badgley) may have been known as “Lonely Boy” on Gossip Girl, but his long list of love interests throughout the series tell a different story.

Of course, no matter how many women he dated, it always came back to Serena van der Woodsen (Blake Lively). Dan and Serena ended up together at the end of Gossip Girl — yes, even after he dated her best friend — but that doesn’t necessarily mean she was the best choice for him.