It's obvious to most Gossip Girl fans, that Serena (Blake Lively) and Dan (Penn Badgley) are one of the end game couples on the iconic series. The pair first got together in the first season, after a young Dan was pining for her. They have been off and on and a consistent presence in each other's lives throughout the seasons. In Season 4, S struggled with the big decision of Nate vs. Dan. Then at the end of the fifth season, she and Dan slept together after he believed Blair was cheating on him. After he found out, she was using him, he told her he never wanted to see her again. But this is Gossip Girl and there is definitely more in store for these two.