Frenemies

Blair and Serena are definitely friends, but are often on edge with one another, clashing over boys, schools, etc. Will they end the second season of Gossip Girl on good terms?
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Dan and Rachel

Dan Humphrey (Penn Badgley) and Rachel Carr (Laura Breckenridge) kiss on Gossip Girl. Scandalous!
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Jack

Jack Bass (Desmond Harrington) in in "In the Realm of the Basses."
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There She Is

L'il Jenny Humphrey in a photo from "O Brother, Where Bart Thou," the December 8, 2008 episode of Gossip Girl. What in the world is J going to throw at us this week?
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Brother and Sister

In this photo from the second-season episode of Gossip Girl, "The Ex-Files," Dan and Jenny share a conversation in their school attire. We like this brother-sister combo.
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In the Play

Dan and Blair in the school play. It was a funny scene.
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Blair, Cyrus and Eleanor

Blair Waldorf, her mom and her new father-in-law in a scene from Gossip Girl. Here's hoping for more Cyrus appearances in Season 3.
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Graduation Day Picture

Chuck Bass and Nate Archibald check their phones in the middle of their high school graduation. Gossip Girl hit them hard with her blast that day!
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Serena van der Woodsen Mug Shot

Serena's mug shot after she was arrested ... thanks to Lily tipping off the cops. That was a story line we didn't see coming.
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Jonathan the Hacker

Eric's boyfriend Jonathan hacked Gossip Girl in the season finale. Did not see that coming.
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The Sad Queen

More and more, we are thinking that the prom does not end happily for the king and queen. But what will come between them?
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Prom Sadness

It's turning into a sad night for this Gossip Girl couple, it would appear. Can Nate and Blair get this turned around?
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Gossip Girl Season 2 Quotes

Serena: Blair will never forgive you for what you did to her.
Chuck: Who told you that little piece of advice, your boyfriend Nate?
Serena: Nate didn't say anything ...
Chuck: Good. I don't think it's wise taking relationship advice from someone in a FAKE relationship. Call me crazy. (pause) Enjoy another night alone with your thoughts.
Serena: Good luck on your suicide mission!

Serena: I still miss Dan sometimes... more than sometimes.
Blair: The only thing lamer than dating Dan Humphrey... is mourning Dan Humphrey.