Season Regulars 9

  1. Blake Lively

    Blake Lively
    Serena van der Woodsen

  2. Leighton Meester

    Leighton Meester
    Blair Waldorf

  3. Penn Badgley

    Penn Badgley
    Dan Humphrey

  4. Chace Crawford

    Chace Crawford
    Nate Archibald

  5. Ed Westwick

    Ed Westwick
    Chuck Bass

  6. Kelly Rutherford

    Kelly Rutherford
    Lily van der Woodsen

  7. Matthew Settle

    Matthew Settle
    Rufus Humphrey

  8. Taylor Momsen

    Taylor Momsen
    Jenny Humphrey

  9. Jessica Szohr

    Jessica Szohr
    Vanessa Abrams

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Crew 1

Writing

Show

Episodes 22

September 14, 2009
0.0

As summer draws to an end, Blair and Chuck continue to adjust to being in a relationship with one another. Serena returns from Europe with new secrets to hide and a new relationship with Carter Baizen. Nate also returns from vacationing and brings home a mysterious girl, Bree Buckley. Meanwhile, Rufus, Dan and Jenny spend the summer in the Hamptons and learn to adjust to the van der Woodsen's glamorous lifestyle

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Crew 2

Directed by: J. Miller Tobin

Written by: Joshua Safran

Guest Stars 13 Full Cast & Crew

  1. Connor Paolo

    Connor Paolo
    Eric van der Woodsen

  2. Sebastian Stan

    Sebastian Stan
    Carter Baizen

  3. James Naughton

    James Naughton
    William van der Bilt

  4. JoAnna Garcia

    JoAnna Garcia
    Bree Buckley

  5. Chris Riggi

    Chris Riggi
    Scott Rosson

  6. Tom Zemon
    Process Server

  7. Matthew Risch

    Matthew Risch
    Ilan (Chief Paparazzi)

  8. Mike Houston

    Mike Houston
    Polo Event Security Guard

  9. Nacho Figueras
  10. Will Blagrove

    Will Blagrove
    Polo Event Valet

  11. Ashley Grace

    Ashley Grace
    Herself

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September 21, 2009
5.0

Blair, determined to have her Queen status at college, starts her first day at NYU along with Dan and Vanessa. However, Georgina, who was assigned as Blair's roommate, sets out to ensure that she does not retain her title. Serena gets ready to move into her dorm at Brown, but has a fight with Chuck before hand. This leads her to search out Chuck's enemy, Carter, to help her get even with him. Meanwhile, Nate and Bree's relationship continues to grow despite the tension their relationship could cause between their families.

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Crew 2

Directed by: Norman Buckley

Written by: Amanda Lasher

Guest Stars 12 Full Cast & Crew

  1. Zuzanna Szadkowski

    Zuzanna Szadkowski
    Dorota Kishlovsky

  2. Michelle Trachtenberg

    Michelle Trachtenberg
    Georgina Sparks

  3. Connor Paolo

    Connor Paolo
    Eric van der Woodsen

  4. Sebastian Stan

    Sebastian Stan
    Carter Baizen

  5. Benita Robledo
  6. Ben Rauch
  7. JoAnna Garcia

    JoAnna Garcia
    Bree Buckley

  8. Chris Riggi

    Chris Riggi
    Scott Rosson

  9. Elena Hurst
  10. Rachael Hip-Flores
    Dorm Girl (as Rachel Hip Flores)

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September 28, 2009
0.0

Blair and Chuck face-off when the both set their sights on an item up for bid at Sotheby's. Serena begins to think that Carter may have returned to his old habits, Georgina becomes interested in Dan, and Vanessa thinks that something is wrong with Scott.

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Crew 2

Directed by: Jean de Segonzac

Written by: Robby Hull

Guest Stars 10 Full Cast & Crew

  1. Michelle Trachtenberg

    Michelle Trachtenberg
    Georgina Sparks

  2. Connor Paolo

    Connor Paolo
    Eric van der Woodsen

  3. Sebastian Stan

    Sebastian Stan
    Carter Baizen

  4. JoAnna Garcia

    JoAnna Garcia
    Bree Buckley

  5. Chris Riggi

    Chris Riggi
    Scott Rosson

  6. Anne Torsiglieri
    Renee Rosson

  7. Andrew Rein
    Hotel Manager

  8. Meghann Fahy
  9. Chriselle Almeida
    NYU Student Aide

  10. Katrina Begin

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October 5, 2009
0.0

During the first day of school at Constance Billard, Jenny takes her place as the new Queen Bee. However, Blair gets in her way. Lily returns home to find that things are not as they were when she left them with Rufus. At NYU, Olivia Burke, an actress, enrolls and is assigned to be Vanessa's roommate.

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Crew 2

Directed by: Mark Piznarski

Written by: John Stephens

Guest Stars 13 Full Cast & Crew

  1. Zuzanna Szadkowski

    Zuzanna Szadkowski
    Dorota Kishlovsky

  2. Connor Paolo

    Connor Paolo
    Eric van der Woodsen

  3. Benita Robledo
  4. Ben Rauch
  5. Valentina de Angelis

    Valentina de Angelis
    Carmen Fortier (as Valentina Deangelis)

  6. Chris Riggi

    Chris Riggi
    Scott Rosson

  7. Jason Heymann
    Photographer

  8. Tory Burch

    Tory Burch
    Herself

  9. Georgina Chapman
  10. Tyra Banks

    Tyra Banks
    Ursula Nyquist

  11. Hilary Duff

    Hilary Duff
    Olivia Burke

  12. Deanna Russo

    Deanna Russo
    K.C. Cunningham

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October 12, 2009
0.0

Lily and Rufus decide to move up their wedding to the next day, but will someone or something come between them before they become man and wife? Chuck discovers a secret that Carter has been keeping from Serena. Dan and Vanessa are pulled into one of Georgina’s schemes. Blair is suspect of Bree and shares her concerns with Nate.

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Crew 2

Directed by: Ron Fortunato

Written by: Leila Gerstein

Guest Stars 9 Full Cast & Crew

  1. Zuzanna Szadkowski

    Zuzanna Szadkowski
    Dorota Kishlovsky

  2. Michelle Trachtenberg

    Michelle Trachtenberg
    Georgina Sparks

  3. Connor Paolo

    Connor Paolo
    Eric van der Woodsen

  4. Sebastian Stan

    Sebastian Stan
    Carter Baizen

  5. Benita Robledo
  6. Valentina de Angelis

    Valentina de Angelis
    Carmen Fortier (as Valentina Deangelis)

  7. JoAnna Garcia

    JoAnna Garcia
    Bree Buckley

  8. Chris Riggi

    Chris Riggi
    Scott Rosson

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October 19, 2009
0.0

Vanessa, hoping to finally win her mother Gabriela’s approval, desperately vies with Blair for the honor of delivering the freshman toast at NYU, but at what price? Dan invites Olivia to meet Rufus and Lily, which leads to all sorts of problems for the new couple. Serena and Nate team up to help Carter Baizen.

Read More

Crew 2

Directed by: John Stephens

Written by: Jake Coburn

Guest Stars 8 Full Cast & Crew

  1. Peyton List

    Peyton List
    Little Girl #1 (as Peyton Roi List)

  2. Sebastian Stan

    Sebastian Stan
    Carter Baizen

  3. Benita Robledo
  4. Samantha Logan

    Samantha Logan
    Little Girl #2

  5. Neal Bledsoe

    Neal Bledsoe
    Josh Ellis

  6. Gina Torres

    Gina Torres
    Gabriela Abrams

  7. Hilary Duff

    Hilary Duff
    Olivia Burke

  8. Shane McRae

    Shane McRae
    PJ Buckley

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October 26, 2009
1.0

In need of publicity for his new hotel, Chuck decides to move up his club’s opening and enlists Serena’s help to get the word out to her celebrity clients. Feeling left out of the planning, Blair attempts to win Chuck’s approval by secretly helping him with a problem concerning opening night. Dan is unnerved when he finally watches one of Olivia’s infamous sex scenes with co-star and real-life boyfriend at the time, Patrick Robinson. Jenny is forced to choose between her relationship with Eric and her new role as Queen Bee. Rufus gets Lily into the Halloween spirit.

Read More

Crew 2

Directed by: Joe Lazarov

Written by: Sara Goodman

Guest Stars 11 Full Cast & Crew

  1. Zuzanna Szadkowski

    Zuzanna Szadkowski
    Dorota Kishlovsky

  2. Connor Paolo

    Connor Paolo
    Eric van der Woodsen

  3. Valentina de Angelis

    Valentina de Angelis
    Carmen Fortier (as Valentina Deangelis)

  4. Elle Fairbanks

    Elle Fairbanks
    Sawyer Bennett

  5. Chuck Cooper

    Chuck Cooper
    Horace Rogers

  6. Simon Miller
    Patrick Roberts

  7. Hilary Duff

    Hilary Duff
    Olivia Burke

  8. Matt Doyle
    Jonathan Whitney

  9. Albert Hammond Jr.
  10. Deanna Russo

    Deanna Russo
    K.C. Cunningham

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November 2, 2009
0.0

Olivia says something she regrets during her appearance on Jimmy Fallon’s talkshow and tries to keep Dan from finding out. With election day around the corner, Nate suspects his grandfather will stop at nothing to get Trip elected to congress. In the midst of another feud with Serena, Blair befriends a new “it” girl and takes her to an election night party at Chuck’s hotel, hoping to make Serena jealous.

Read More

Crew 2

Directed by: Mark Piznarski

Written by: Lenn K. Rosenfeld

Guest Stars 11 Full Cast & Crew

  1. Benita Robledo
  2. Aaron Tveit

    Aaron Tveit
    Trip van der Bilt

  3. Holley Fain

    Holley Fain
    Maureen van der Bilt

  4. Annika Pergament
  5. Bree Williamson

    Bree Williamson
    Brandeis

  6. James Naughton

    James Naughton
    William van der Bilt

  7. Simon Miller
    Patrick Roberts

  8. Chip Brookes

    Chip Brookes
    Campaign Strategist

  9. Hilary Duff

    Hilary Duff
    Olivia Burke

  10. Jimmy Fallon

    Jimmy Fallon
    Jimmy Fallon

  11. Deanna Russo

    Deanna Russo
    K.C. Cunningham

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0.0

Jenny wants to be the Queen Bee of not only Constance but of all the Upper East Side, as she lands the hottest escort for the Cotillion. Meanwhile Dan and Vanessa try to convince Olivia to stay in NY by showing her the "true college experience". Leighton Meester's new single "Somebody to Love" is featured in the episode, along with performance from Plastiscines.

Read More

Crew 2

Directed by: Alison Maclean

Written by: Amanda Lasher

Guest Stars 12 Full Cast & Crew

  1. Connor Paolo

    Connor Paolo
    Eric van der Woodsen

  2. Ben Rauch
  3. Aaron Tveit

    Aaron Tveit
    Trip van der Bilt

  4. Valentina de Angelis

    Valentina de Angelis
    Carmen Fortier (as Valentina Deangelis)

  5. Elle Fairbanks

    Elle Fairbanks
    Sawyer Bennett

  6. Pedro Barreira
    Hugh Gilles

  7. Ryan Vigilant
    Graham Collins

  8. Beth Fowler
    Mistress of Ceremonies

  9. Wolé Parks

    Wolé Parks
    Staffer

  10. Sarah Steele

    Sarah Steele
    Kira Abernathy

  11. Hilary Duff

    Hilary Duff
    Olivia Burke

  12. Matt Doyle
    Jonathan Whitney

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November 16, 2009
0.0

Hoping to impress the elitist theater kids at NYU, Blair sets her sights on landing a private concert with the hottest musical performer of the year, Lady Gaga. Dan and Olivia sign up to write and star in a school play, based on an idea by Blair and directed by Vanessa. With Blair out of the picture, Serena turns to Nate to help her get through a difficult situation. As a favor to Chuck, Jenny agrees to hang out with Damien, the son of an ambassador who is staying at Chuck's hotel, but the experience proves to be a lot more intriguing than she expected.

Read More

Crew 2

Directed by: Tony Wharmby

Written by: Leila Gerstein

Guest Stars 9 Full Cast & Crew

  1. Benita Robledo
  2. Erich Bergen

    Erich Bergen
    Paul Hoffman

  3. Ben Rauch
  4. Aaron Tveit

    Aaron Tveit
    Trip van der Bilt

  5. Holley Fain

    Holley Fain
    Maureen van der Bilt

  6. Kate Goehring
    Housekeeper

  7. Lady Gaga

    Lady Gaga
    Herself

  8. Kevin Zegers

    Kevin Zegers
    Damian Daalgard

  9. Hilary Duff

    Hilary Duff
    Olivia Burke

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