Dan and anyone, 'Gossip Girl'

Penn BadgleyBlake LivelyChace CrawfordMichelle TrachtenbergHilary Duff
Poor Dan Humphrey (Penn Badgley), he always comes off as the brother or the friend -- kind of asexual actually. He and Serena (Blake Lively) definitely had the sibling vibe going on, and now that they're related by marriage, that's too close for comfort. Dan and Vanessa (Jessica Szohr), Dan and... The CW
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