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- Season 2 overviewSep 1, 2008-May 18, 200925 episodesSeason 2 episodes1. Summer, Kind of Wonderful Sep 1, 2008
- Serena and Nate pretend they are a couple to cover up Nate's relationship with a married woman.
- 2. Never Been Marcused Sep 8, 2008
- Dan and Serena decide to keep their recent hook-ups a secret.
- 3. The Dark Night Sep 15, 2008
- Serena and Dan are forced to deal with their problems when a blackout traps them in an elevator.
- 4. The Ex-Files Sep 22, 2008
- Serena notices Dan cozying up to the new girl in school; Vanessa uncovers a scandalous secret.
- 5. The Serena Also Rises Sep 29, 2008
- Dan begins hanging out with Chuck; Lily discovers that her husband has been keeping a secret.
- 6. New Haven Can Wait Oct 13, 2008
- Serena ditches plans to visit Brown and accepts an invitation to visit Yale.
- 7. Chuck in Real Life Oct 20, 2008
- Vanessa blackmails Blair into being a nicer person; Blair entices Chuck to seduce Vanessa.
- 8. Pret-a-Poor-J Oct 27, 2008
- Jenny makes friends with a model who encourages her to confront Eleanor Waldorf.
- 9. There Might Be Blood Nov 3, 2008
- Serena discovers that Aaron has been keeping a secret from her.
- 10. Bonfire of the Vanity Nov 10, 2008
- Blair despises Eleanor's new boyfriend; Jenny moves in with Agnes.
- 11. The Magnificent Archibalds Nov 17, 2008
- Blair is upset when her mother's boyfriend ruins all of her favorite Thanksgiving traditions.
- 12. It's a Wonderful Lie Dec 1, 2008
- Blair and Chuck make a bet that they can find the perfect dates for each other.
- 13. O Brother, Where Bart Thou? Dec 8, 2008
- Tragedy strikes the lives of the Upper East Side teens and their parents.
- 14. In the Realm of the Basses Jan 5, 2009
- Uncle Jack Bass arrives in town to try and help Chuck pick up the pieces.
- 15. Gone With the Will Jan 12, 2009
- Lily, Bart's brother, Jack, and Chuck learn the fate of the Bass empire.
- 16. You've Got Yale! Jan 19, 2009
- Chuck teams up with an unlikely ally in his war against Jack.
- 17. Carnal Knowledge Feb 2, 2009
- Chuck wakes up in a hotel with little memory of what happened the previous evening.
- 18. The Age of Dissonance Mar 16, 2009
- Dan and Rachel have a hard time staying away from each other.
- 19. The Grandfather Mar 23, 2009
- Devastated Blair explores her dark side; Lily and Rufus decide to be honest with each other.
- 20. Remains of the J Mar 30, 2009
- Serena decides to plan a small party for Jenny's 16th birthday.
- 21. Seder Anything Apr 20, 2009
- Serena returns from her trip with Gabriel and Poppy; Blair and Nate's grandfather make a deal.
- 22. Southern Gentlemen Prefer Blondes Apr 27, 2009
- Georgina Sparks returns after undergoing a transformation; Nate and Chuck come to a crossroads.
- 23. The Wrath of Con May 4, 2009
- Blair pressures Georgina into helping her with a scheme; Chuck and Nate's rivalry comes to a head.
- 24. Valley Girls May 11, 2009
- Lily remembers getting kicked out of boarding school when she was 17.
- 25. The Goodbye Gossip Girl May 18, 2009
- Gossip Girl shakes things up by sending out a damaging e-mail blast during commencement.