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Dan's GG kissing history includes (l-r) Olivia (Hilary Duff), Vanessa (Jessica Szohr) and Serena (Blake Lively).
For someone who sees himself as a sensitive, artsy outcast, Dan Humphrey (Penn Badgley) sure gets around. As his flirtation with Blair (Leighton Meester) heats up, here’s a look back at the many (many, many) other ladies who have caught Lonely Boy’s eye over the past four seasons of Gossip Girl.
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