Season Two is the second season of Gossip Girl, the American teen drama based upon the book series by Cecily von Ziegesar. Developed for television by Josh Schwartz and Stephanie Savage. It aired on the CW from September 1st, 2008 until May 18th, 2009 with 25 episodes.
- The newly created Bass-Van der Woodsen family, known as the wealthiest on the Upper East Side, and their ups and downs.
- The marriage of Eleanor Waldorf and Cyrus Rose, causing Blair to struggle with her new blended family.
- Jenny's rebellion from "Little J" and attempting to start her own clothing line.
- Dan is accepted to Yale, but has to refuse due to financial stress and ends up at NYU along with Vanessa. Serena is also accepted, but denies to attend Brown University. Blair is rejected by Yale, but is able to get into NYU with Cyrus' help. Nate plans to attend Columbia University.
- Nate accepts money from a married Duchess, Catherine Beaton, to save his family from debt.
- Bart Bass tragically dies in a car accident. Rufus and Lily rekindle their relationship after his death.
- Lily adopts Chuck, becoming his legal guardian, so that she could be named head of Bass Industries and give it to Chuck when he is of age.
- Serena, Eric, Dan, and Jenny discover Lily and Rufus had a lovechild and they are related through their unknown half-brother.
- Blair and Chuck struggle with admitting their feelings for one another.
- Blake Lively as Serena van der Woodson (Appears in 25/25 episodes)
- Leighton Meester as Blair Waldorf (Appears in 25/25 episodes)
- Penn Badgley as Dan Humphrey (Appears in 25/25 episodes)
- Chace Crawford as Nate Archibald (Appears in 22/25 episodes)
- Ed Westwick as Chuck Bass (Appears in 25/25 episodes)
- Jessica Szohr as Vanessa Abrams (Appears in 18/25 episodes)
- Taylor Momsen as Jenny Humphrey (Appears in 25/25 episodes)
- Kelly Rutherford as Lily van der Woodson (Appears in 19/25 episodes)
- Matthew Settle as Rufus Humphrey (Appears in 25/25 episodes)
- Kristen Bell as Gossip Girl (character) (Voice only and uncredited, 25/25 episodes)
- Connor Paolo as Eric van der Woodsen
- Margaret Colin as Eleanor Waldorf
- Zuzanna Szadkowski as Dorota Kishlovsky
- Michelle Trachtenberg as Georgina Sparks
- Amanda Setton as Penelope Shafai
- Tamara Feldman as Poppy Lifton
- Desmond Harrington as Jack Bass
- Sebastian Stan as Carter Baizen
- Wallace Shawn as Cyrus Rose
- John Shea as Harold Waldorf
- Dreama Walker as Hazel Williams
- Nicole Fiscella as Isabel Coates
- Yin Chang as Nelly Yuki
- Robert John Burke as Bart Bass
- John Patrick Amedori as Aaron Rose
- Caroline Lagerfelt as CeCe Rhodes
- Mädchen Amick as Catherine Beaton
- Patrick Heusinger as Marcus Beaton
- Artie Hammer as Gabriel Edwards
- Aaron Tveit as Tripp van der Bilt
- Francie Swift as Anne Archibald
- Sam Robards as Howard "The Captain" Archibald
- Willa Holland as Agnes Andrews
- Matt Doyle as Jonathan Whitney
- William Abadie as Roman Garrel
- Laura Breckenridge as Rachel Carr
- Jan Maxwell as Headmistress Queller
- James Naughton as William van der Bilt
- Laura Leigh as Amanda Lasher
- David Patrick Kelley as Noah Shapiro
- Jill Flint as Bex Simon
- Michelle Hurd as Laural
- Cyndi Lauper as Herself
Valley Girls (TV series) Pilot
- Brittany Snow as Lily Rhodes
- Krysten Ritter as Carol Rhodes
- Cynthia Watros as Celia "CeCe" Rhodes
- Andrew McCarthy as Rick Rhodes
- Matt Barr as Keith Van Der Woodsen
|01||Summer Kind of Wonderful||September 1, 2008||3.43|
|As the summer draws to a close in the Hamptons, Serena and Nate have everyone fooled into thinking they are a couple; to cover up the fact that Nate has been having an affair with an older woman. Blair returns from abroad with a hot guy on her arm, making a very jealous Chuck question his decision to stop pursuing Blair. Meanwhile, Dan has spent the summer assisting a famous author, but finds himself preoccupied with Serena, leading him to take a risk. While interning for Eleanor Waldorf's company, Jenny procures an invite to the much-anticipated Hampton's White Party, with the help of Eric van der Woodsen.
|02||Never Been Marcused||September 8, 2008||3.25|
|Blair is over the moon that she is dating royalty and has every intention of becoming a royal herself, but a scheming Chuck has other plans for Blair and her new love, Marcus. Serena and Dan agree to keep their recent hook-ups a secret from their friends and family until they figure out what all this means for their relationship. Meanwhile, Nate learns the downside to having an affair with an older, married woman.
|03||The Dark Night||September 15, 2008||3.73|
|Blair questions the lack of passion in her relationship with Marcus, while at the same time Chuck appears to have lost his passion for every woman other than Blair. Meanwhile, Nate struggles between his feelings for Vanessa and his complicated relationship with Catherine. Jenny risks losing her internship when Eleanor catches her crossing the line. Stuck in an elevator due to a blackout, Dan and Serena talk about their relationship and land on a surprising decision.
|04||The Ex-Files||September 22, 2008||3.33|
|On the first day of school, Blair and her minions decide to befriend the new girl Amanda in order to sabotage her and steer her from dating Dan. Vanessa discovers a scandalous secret about Catherine and enlists Blair's scheming expertise to use the information to help Nate. Meanwhile, Lily finds herself drawn back to her ex, Rufus, once again.
|05||The Serena Also Rises||September 29 2008||3.40|
|In the midst of Fashion Week, a furious Blair learns that her mother, Eleanor, has given Serena and her new socialite friend, Poppy Lifton, front row seats to her fashion show and decides to sabotage the event. Meanwhile, Dan starts hanging out with Chuck, but learns the hard way that a walk on the dark side has many risks and Lily discovers a secret that Bart has been keeping from her.
|06||New Haven Can Wait||October 13, 2008||3.31|
|Following a fight between Blair, Serena decides to get even by ditching her plans to visit Brown and accepting a personal invitation from the Dean of Yale to visit the school. After discovering that his recommendation letters for Yale were never submitted, Dan frantically tries to figure out a way to salvage any change of getting accepted into the school. While visiting Yale, Chuck is kidnapped by a group of Skull and Bones members and Nate hooks up with a student who may hold the key to Dan's acceptance.
|07||Chuck in Real Life||October 20, 2008||3.03|
|Vanessa blackmails Blair into helping her with a cause, which leads to Blair seeking revenge along with Chuck. Meanwhile, Lily and Bart throw an extravagant housewarming party but a rebellious Serena is not ready to play by their rules. Also, Dan and Jenny discover a big secret Nate has been keeping from his friends.
|08||Pret-a-Poor-J||October 27, 2008||3.05|
|Jenny befriends a young model, Agnes, who encourages her to explore her wild side, and take some risks with her life. Meanwhile, Serena meets an artist, Aaron Rose, whom she has an instant attraction to. Blair attempts to seduce Chuck, but it proves tougher than she ever could have imagined.
|09||There Might be Blood||November 3, 2008||3.16|
|Serena discovers a secret that Aaron has been keeping from her, and begins to question whether he is the guy she thought he was. Hoping it will help her chances of getting into Yale, Blair naively agrees to babysit the 15-year-old daughter of a prominent Yale donor. When the teenager proves to be more than a handful, Blair begins to suspect that the events of the evening may end up hurting her chances of getting into her dream school. Meanwhile, Jenny and Agnes plan a guerrilla fashion show that will either launch Jenny's fashion career, or ruin her chances of ever being accepted.
|10||Bonfire of the Vanity||November 10, 2008||2.88|
|Blair does not approve of the new man in her mother's life and she makes it her mission to break up the two by any means necessary. Jenny moves in with Agnes as they move forward with their plans for a fashion line. Serena continues to fall for the new guy in her life, Aaron, but she discovers something about him that threatens to end things just as they were getting started. Dan tries to win the trust of Bart in order to expose him to further his writing career but things heat up after Chuck realizes the true reason Dan is spending so much time around his family.
|11||The Magnificent Archibalds||November 17, 2008||2.89|
|Thanksgiving in the Waldorf household gets off to a rough start as Blair finds that her mother's boyfriend is getting in the way of her favorite traditions. Meanwhile, Lily finds herself trying to broker a peace treaty between Rufus and Jenny, and Serena is not quite ready to come clean with Aaron about her complicated past. Vanessa and Chuck come to Nate's aid when he is again being forced to confront his father's crimes. Finally, Eric discovers a secret that Bart has been keeping from Lily.
|12||It's a Wonderful Lie||December 1, 2008||3.11|
|For the annual Snowflake Ball, Blair and Chuck make a bet that they can find ideal dates for each other. Aaron's ex-girlfriend, Lexi, expresses an interest in Dan. Nate, Jenny, and Vanessa get into a sticky situation that puts their friendships and hearts on the line. Also, a sudden and tragic event will rock the world of everyone in the city.
|13||O Brother, Where Bart Thou?||December 8, 2008||2.99|
|Following the death of Bart Bass, Blair decides she has something important to say to Chuck, but soon realizes it's not a good time. When Serena decides to travel to Argentina with Aaron, Dan decides to express his feelings for her. Meanwhile, Cyrus and Eleanor take a huge step in their relationship and Rufus discovers something that Lily has been keeping from everybody for a long time.
|14||In the Realm of the Basses||January 5, 2009||2.96|
|Chuck's uncle Jack arrives on the Upper East Side to assist him with picking up the messy pieces of his father's passing. Trying her best to forget her last painful exchange with Chuck, Blair focuses her attention on being accepted into the most prestigious ladies club in the city. Jenny returns to Constance Billard and immediately takes on Penelope and her posse of mean girls. Meanwhile, Serena and Dan make a decision about their future.
|15||Gone with the Will||January 12, 2009||2.85|
|With the reading of Bart Bass' will, Chuck, Jack, and Blair learn the fate of the Bass empire. Meanwhile, Rufus and Lily's relationship becomes strained as Rufus seeks details about the child he never knew he had. Noticing that his father is acting strange, Dan does some investigating of his own and discovers Rufus and Lily's secret and becomes unsure what to do with it.
|16||You've Got Yale!||January 19, 2009||2.22|
|It's that time of year when Constance Billard and St. Jude's students find out who is and isn't worthy of early admission to Yale University. Serena bonds with her new teacher, Rachel Carr, who quickly becomes an enemy of Blair's. Meanwhile, Chuck pairs up with an unlikely ally in his war with Jack over Bass Industries while Nate and Vanessa have a romantic night at the opera.
Title based off of the movie You've Got Mail.
|17||Carrnal Knowledge||February 2, 2009||2.31|
|In retaliation for not playing by the unspoken rules of Constance Billard, Blair hatches a plan to bring down her teacher, Rachel. After Chuck wakes up in a hotel and only has a minor recollection of what happened the previous evening, Nate and Vanessa try to help him fill in the missing pieces. Meanwhile, Dan and Rachel consummate their relationship after everything changes.
|18||The Age of Dissonance||March 16, 2009||2.33|
|The seniors put on a production of The Age of Innocence and find their personal lives mirroring the play. Serena develops a crush on the play's director, Julian, and enlists Vanessa's knowledge of theater to help her get his attention. Blair receives devastating news about her future that leads her on a witch-hunt for the person responsible. Dan and Rachel agree to stay away from each other but find the promise hard to keep. Meanwhile, Chuck tries to help a new friend, but has to involve a rival from his past.
|19||The Grandfather||March 23, 2009||2.25|
|Devastated by the recent plot twist in her life, Blair turns her back on her prestigious way of life in favor of a more wild and unpredictable lifestyle, causing Serena and Chuck to have serious concerns about their friend. Vanessa convinces Nate that it may be time to forgive and forget when it comes to his mother's family, who abandoned Nate after his father's scandal. In a misguided effort to be completely honest with each other, Lily and Rufus agree to share lists of their past lovers.
|20||Remains of the J||March 30, 2009||2.45|
|Serena decides to throw Jenny a party for her sixteenth birthday, but things get way out of control when the party is turned into a teenage rager. In a moment of weakness, Vanessa agrees to help Chuck with a scheme having to do with Blair and Nate. Meanwhile, Rufus learns that Dan will not receive financial aid at Yale and tries to figure out another way to cover the cost of his education.
|21||Seder Anything||April 20, 2009||2.37|
|Serena returns from her trip to Spain with a secret. Blair makes a secret deal with Nate's grandfather, William, and Nate learns some disturbing information about his father's arrest. Dan takes a job as a cater-waiter to earn money for college, but is distressed when he discovers the gig is a Passover seder at the Waldorf penthouse and several of his friends and family are guests.
|22||Southern Gentlemen Prefer Blondes||April 27, 2009||1.97|
|Georgina Sparks returns to the Upper East Side after undergoing a major transformation. Chuck and Nate find themselves at a major crossroads in their friendship as it pertains to their mutual interest in Blair. Serena finds her relationship with Gabriel growing more complicated.
|23||The Wrath of Con||May 4, 2009||2.22|
Blair pressures Georgina into making amends for her past bad behavior by helping in a scheme. The rivalry between Nate and Chuck over Blair comes to a head. Meanwhile, Lily hatches a secret plan to help Rufus with Dan's college tuition.
|24||Valley Girls||May 11, 2009||2.30|
|In a flashback to the 80s, 17-year-old Lily Rhodes (Brittany Snow) gets kicked out of boarding school and runs away to Santa Barbara, where she reconnects with her parents, Rick (Andrew McCarthy) and CeCe (Cynthia Watros). Afterwards, she goes to find her rebellious sister, Carol (Krysten Ritter). Back in present day, Blair and Nate attend prom together, but the evening doesn't turn out exactly as planned. Meanwhile, Serena and Lily don't see eye to eye over Serena's recent run in with the law.
|25||The Goodbye Gossip Girl||May 18, 2009||2.23|
|Gossip Girl decides to liven things up at graduation by sending out a shocking and damaging email blast, stirring Serena to come up with a plan of attack. Meanwhile, Lily and Rufus reconcile and decide to take a big step, Chuck decides to make a revelation, and Nate plans to spend his summer rebelling against his family.
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