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.

There was also a spin-off pilot, Valley Girls; focusing on Lily van der Woodsen (Kelly Rutherford/Brittany Snow) and her family in California.

Notable Plots

  • 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.


Main Cast

Recurring/Guest Cast

Valley Girls (TV series) Pilot


# Image Title Airdate Viewers
01 Summerkindport 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.

The title of the episode is based off of the movie title, "Some Kind of Wonderful."

02 NeverBeenMarcusedport 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.

The title of the episode is based off of the movie title, "Never Been Kissed."

03 Darknightport 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.

The title of the episode is based off of the movie title, "The Dark Knight."

04 Exfilesport 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.

The title of the episode is based off of the movie title, "The X-Files."

05 Serenarisesport 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.

The title of the episode is based off of the movie title, "The Sun Also Rises."

06 Newhavenport 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.

The title of the episode is based off of the movie title, "Heaven Can Make."

07 Chuckport 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.

The title of the episode is based off of the movie title, "Dan in Real Life."

08 Poorjennyport 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.

The title of this episode is based off of the movie title, "Prêt-à-Porter."

09 ThereMightBeBloodport 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.

The title of the episode is based on the movie title, "There Will Be Blood."

10 Bonfareport 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.

The title of the episode is based off of the movie title, "Bonfire of the Vanities."

11 Archibaldsport 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.

The title of this episode is based off of the movie title, "The Magnificent Ambersons."

12 Lieport 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.

The title of the episode is based off of the movie title, "It's a Wonderful Life."

13 Obrotherport 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.

The title of the episode is based off of the movie title, "O Brother, Where Art Thou."

14 Intherealmport 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.

The title of the episode is based off of the movie title, "Ai no corrida (In the Realm of the Senses)."

15 Gonewillport 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.

The title of this episode is based off of the movie title, "Gone with the Wind."

16 Ugotyaleport 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 Carnalknowlegeport 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.

Title based off of the movie Carnal Knowledge.

18 Agedisport 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.

Title based off of the movie The Age of Innocence.

19 Grandfatherport 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.

Title based off of the movie The Godfather (Part I).

20 Remainport 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.

Title based off of the movie The Remains of the Day

21 Sederport 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.

Title based off of the movie Say Anything

22 Southernblondeport 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.

Title based off of the movie Gentlemen Prefer Blondes

23 Wrathport 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.

Title based off of the movie Star Trek: The Wrath of the Khan.

24 Valleygirlport 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.

Title based off of the movie Valley Girl.

25 Goodbyeport 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.

Title based off of the movie The Goodbye Girl

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