Season 5: How to Lose Friends and Alienate Family
In the beginning: Serena is working as a production assistant in Hollywood. Chuck and Nate visit her. Hilarity ensues.
Hook-ups: That whole Max thing... Funny how Serena always seems to be the last to know about a good scam. Turns out, he's her fake cousin's crazy ex-boyfriend. OOPS! And we thought Blair was the one who was unlucky in love...
Feuds: Dan, Charlie/Ivy, Diana Payne, Lola (S almost makes her It girl, tries to take it back...), Blair... Pretty much everyone has issues with everyone this season
Scandals: Dan's book threatens friends' relationships and causes problems in her job — she has to choose between her feelings about D and her job.; Serena plays Gossip Girl.
Relationship with Blair: They actually seem pretty good for most of the season... until Serena becomes Gossip Girl and exposes stuff about B and Blair finds out
Relationship with Dan: Serena realizes she still has feelings for Dan but she sees that he likes Blair, which totally sucks. In fact, it's super awkward to watch. At Blair's wedding, she says ""I love you Dan Humphrey, always have, always will" and what does Dan say? Nothing. In the end, he tells her he never wants to see her again. Sometimes on GG that's code for "not until we fall in love next season.” In this case, who knows?
Biggest Moment: Where do we begin? Realizing she loves Dan and telling him? Lying a million times? There's no real moment of "AHA!" for S this season and no single moment that destroys her. The worst thing that happens is that she consistently destroys friendships, one by one, which sets up a clear path for her to leave town.
And in the end?: Serena leaves town with one of Damian Dalgaard's drug dealers, on a train in a very S way of fleeing.