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Season 2 |
| 19 :02x01 - Summer, Kind of Wonderful (Sep/01/2008) | | In the second season premiere, the gang heads up to the Hamptons to escape from the summer heat. There, Blair tries to make Chuck jealous by hooking up with another guy. Meanwhile, Nate finds a steamy hook-up of his own and Serena questions her relationship with Dan. Back in the Upper East Side, Dan lands a job at a library. | | Guest Stars: Jay McInerney as Himself, Madchen Amick as Duchess Catherine Beaton, Tinsley Mortimer as Herself, Michelle Hurd as Laurel, Patrick Heusinger as Lord Marcus Beaton, Caroline Lagerfelt as Celia 'CeCe' Rhodes, Catherine Haena Kim as Unknown, Paloma Guzman as Unknown, Connor Paolo as Eric van der Woodsen, | Co-Guest Stars: Ashley Cook as Brazilian Beauty, Alexandra Carl as Laurel's Assistant | Director: J. Miller Tobin
Writer: Joshua Safran | | Songs: Shwayze -- Buzzin', -- Crazy, Motion City Soundtrack -- Fell In Love Without You (acoustic), Teyana Taylor -- Google Me, The Windupdeads -- Reverse of Shade | | | |
| 20 :02x02 - Never Been Marcused (Sep/08/2008) | | Blair, excited over the fact that she is dating royalty, is unaware of Chuck's scheming to break up her and her new love interest, Marcus. Serena and Dan agree to keep their relationship problems a secret from their friends and family until they can figure out their future. Meanwhile, Nate begins to find the downside to having an affair with an older woman. | | Guest Stars: Zuzanna Szadkowski as Dorota, Francie Swift as Anne Archibald, Patrick Heusinger as Lord Marcus Beaton, Madchen Amick as Duchess Catherine Beaton | Director: Michael Fields (1)
Writer: Stephanie Savage | | Songs: Carolina Liar -- Beautiful World, The Pierces -- Boy in a Rock and Roll Band, Seabear -- Cat Piano, The Fratellis -- Chelsea Dagger, Katie Herzig -- Forevermore, LCD Soundsystem -- New York, I Love You But You're Bringing Me Down, The Fratellis -- Tell Me a Lie | | | |
| 21 :02x03 - The Dark Night (Sep/15/2008) | | Serena and Dan must face their problems when they are trapped in an elevator together during a blackout. Meanwhile, Blair begins to question the lack of passion in her new relationship with Marcus as Chuck's passion for women is lost on everyone but Blair. Elsewhere, Nate must choose between his feelings for Vanessa and for Catherine. | | Guest Stars: Amanda Setton as Penelope, Michelle Hurd as Laurel, Yin Chang as Nelly Yuki, Margaret Colin as Eleanor Waldorf, Madchen Amick as Duchess Catherine Beaton, Patrick Heusinger as Lord Marcus Beaton | Director: Janice Cooke (1)
Writer: John Stephens | | Songs: Manchester Orchestra -- I Can Feel a Hot One, Santogold -- Lights Out | | | |
| 22 :02x04 - The Ex-Files (Sep/22/2008) | | When Serena sees Dan with Amanda, the new girl in school, Blair takes it upon herself to have her circle of friends befriend Amanda and end her budding relationship with Dan. Meanwhile, Vanessa uncovers a scandalous secret about Catherine and enlists Blair's help in using the information to help Nate; and Lily finds herself drawn to Rufus. | | Guest Stars: Amanda Setton as Penelope, Michelle Hurd as Laurel, Nicole Fiscella as Isabel Coates, Yin Chang as Nelly Yuki, Patrick Heusinger as Lord Marcus Beaton, Connor Paolo as Eric van der Woodsen, Madchen Amick as Duchess Catherine Beaton, Laura-leigh as Amanda | Director: Jim McKay
Writer: Robert Hull | | Songs: The Republic Tigers -- Building and Mountains, MGMT -- Electric Feel, Nappy Roots -- Good Day, The Little Ones -- Morning Tide, Cloud Cult -- Please Remain Calm, Santogold -- Shove It, Chris Chavez -- The Observer | | | |
| 23 :02x05 - The Serena Also Rises (Sep/29/2008) | | During Fashion Week, Blair learns that Eleanor, after a suggestion from Jenny, has given Serena and Poppy front row seat to the Waldorf show. Hurt, Blair decides to sabotage the show. Meanwhile, Dan begins hanging out with Chuck, but Dan learns the hard way that Chuck isn't the best company to keep. Elsewhere, Lily finds out the dark secret that Bart has been keeping. | | Guest Stars: Amanda Setton as Penelope, Dreama Walker as Hazel, Michelle Hurd as Laurel, Zuzanna Szadkowski as Dorota, Michael Kors as Himself, Tinsley Mortimer as Herself, Jill Flint as Bex Simon, Nicole Fiscella as Isabel Coates, Margaret Colin as Eleanor Waldorf, Tamara Feldman as Poppy Lifton, Robert John Burke (3) as Bart Bass, Cristina Greeven Cuomo as Herself, David Patrick Kelly (1) as Noah Shapiro, Yin Chang as Nelly Yuki | Director: Patrick Norris
Writer: Jessica Queller | | Songs: Nous Non Plus -- Fille atomique, The Republic Tigers -- Made Concrete, Lady GaGa -- Poker Face, Phantom Planet -- Raise the Dead, The Duke Spirit -- This Ship Was Built to Last | | | |
| 24 :02x06 - New Haven Can Wait (Oct/13/2008) | | When Blair and Serena get into a fight, Serena decides to get back at Blair by visiting Yale, Blair's dream school, instead of Brown. Meanwhile, Dan learns that his letters of recommendation were never sent to Yale and scrambles to find a way to make sure is chances of getting into the Ivy League school have not been damaged. At Yale, Chuck is taken captive my members of the Skull and Bones society and Nate hooks up with a Yale co-ed. | | Guest Stars: Zuzanna Szadkowski as Dorota, Matt Burns as Leader of the Yale Skull and Bones, Reed Birney as Mr. Prescott, Byron Jennings as Dean Berube, Margaret Colin as Eleanor Waldorf, Krysta Rodriguez as Jordan Steele | Director: Norman Buckley
Writer: Joshua Safran, Alexandra McNally | | | |
| 25 :02x07 - Chuck In Real Life (Oct/20/2008) | | Vanessa uses the picture she has of Catherine and Marcus together in order to blackmail Blair into being a better person. However, Blair gets back at Vanessa by having Chuck seduce her. Lily and Bart throw a housewarming party and expect their children to behave in front of the press, but Serena does not do so. Meanwhile, Dan and Jenny uncover a secret Nate has been keeping. | | Guest Stars: Amanda Setton as Penelope, Nicole Fiscella as Isabel Coates, Charles Cooper as Horace, Ariel Foxman as Herself, Honor Brodie as Herself, Matt Doyle as Jonathan, Connor Paolo as Eric van der Woodsen, Robert John Burke (3) as Bart Bass | Director: Tony Wharmby
Writer: Lenn K. Rosenfeld | | | |
| 26 :02x08 - Pret-A-Poor-J (Oct/27/2008) | | Jenny befriends Agnes, a young model, who encourages Jenny to confront her boss, Eleanor Waldorf who has been "borrowing" her designs. Serena and Dan attend Rufus' art opening as friends, but the situation becomes uncomfortable for the both of them when Serena hits it off with Aaron, an artist. Meanwhile, Blair tries to seduce Chuck, but finds it to be more difficult than expected. | | Guest Stars: Zuzanna Szadkowski as Dorota, Margaret Colin as Eleanor Waldorf, Wade Allain-marcus as Max, John Patrick Amedori as Aaron Rose, Willa Holland as Agnes Andrews | Director: Vondie Curtis-Hall
Writer: Amanda Lasher | | Songs: Robyn -- Crash and Burn Girl, Turin Brakes -- Dark On Fire, t.A.T.u. -- How Soon Is Now?, Black Kids -- Partie Traumatic, Alain Whyte -- Robot Talk, Mad Staring Eyes -- Walking in the Streets, Princess One Point Five -- With Light There is Hope | | | | | | |
| 28 :02x10 - Bonfire of the Vanity (Nov/10/2008) | | Blair sets out on a mission to break up her mother and Cyrus Rose, her new man. Jenny moves in with Agnes as the two continue with their plans for their own fashion line. As Serena continues to fall for Aaron, she learns something that may derail their relationship forever while Dan interviews Bart Bass for an article for Vanity Fair. | | Guest Stars: Dreama Walker as Hazel, Zuzanna Szadkowski as Dorota, Daniel Stewart Sherman as Deep Throat, Amanda Setton as Penelope, Peter Francis James (1) as James Wolf, Nicole Fiscella as Isabel Coates, Yin Chang as Nelly Yuki, Brennan Brown as Mr. Smith, Cyndi Lauper as Herself, Wallace Shawn as Cyrus Rose, Margaret Colin as Eleanor Waldorf, Willa Holland as Agnes Andrews, John Patrick Amedori as Aaron Rose, Robert John Burke (3) as Bart Bass, David Patrick Kelly (1) as Noah Shapiro | Director: David Von Ancken
Writer: Jessica Queller | | Songs: Kings of Leon -- Closer, Kings of Leon -- Sex on Fire | | | |
| 29 :02x11 - The Magnificent Archibalds (Nov/17/2008) | | It's Thanksgiving and Blair is upset that Cyrus, her mother's new boyfriend, has decided to ruin their holiday traditions. Lily finds herself in the middle of Rufus and Jenny, who threatens to stop talking to her father if things do not go her way. Serena continues to hide her complicated past from Aaron, but Dan ends up accidently revealing parts to him. Meanwhile, Blair and Chuck come to Nate's aid when he has to confront his father; and Eric learns of a secret that Bart is keeping from his mother. | | Guest Stars: Zuzanna Szadkowski as Dorota, Dion Graham as FBI Agent, Francie Swift as Anne Archibald, Margaret Colin as Eleanor Waldorf, John Shea (1) as Harold Waldorf, Connor Paolo as Eric van der Woodsen, Robert John Burke (3) as Bart Bass, Sam Robards as Howie "The Captain" Archibald, John Patrick Amedori as Aaron Rose, Wallace Shawn as Cyrus Rose | Director: Jean de Segonzac
Writer: Joshua Safran | | | |
| 30 :02x12 - It's a Wonderful Lie (Dec/01/2008) | | As the annual Snowflake Ball approaches, Blair and Chuck make a bet that they can find the perfect date for one another. Aaron's ex-girlfriend, Lexi, becomes attracted to Dan, creating mixed feelings for Serena. | | Guest Stars: Zuzanna Szadkowski as Dorota, Dreama Walker as Hazel, Jake O'connor as Chuck 2.0, Nicole Fiscella as Isabel Coates, Robert John Burke (3) as Bart Bass, Jennifer Damiano as unknown, Natalie Knepp as Lexi, John Patrick Amedori as Aaron Rose | Director: Patrick Norris
Writer: Robert Hull | | | | | | |
| 32 :02x14 - In the Realm of the Basses (Jan/05/2009) | | Uncle Jack arrives in New York to help Chuck following his father's death, but must find him first. Blair, trying to forget her fight with Chuck, turns her attention to getting accepted to the Colony Club. | | Guest Stars: Zuzanna Szadkowski as Dorota, Dreama Walker as Hazel, Nicole Fiscella as Isabel Coates, Yin Chang as Nelly Yuki, Linda Emond as Headmistress Queller, Connor Paolo as Eric van der Woodsen, Amanda Setton as Penelope, Desmond Harrington as Jack Bass | Director: Tony Wharmby
Writer: John Stephens | | Songs: White Lies -- E.S.T. | | | |
| 33 :02x15 - Gone with the Will (Jan/12/2009) | | Chuck, Jack and Lily come together for the reading of the will which reveals what will come of the Bass empire. Rufus and Lily's relationship is put on hold as Rufus searches for the child he never knew he had. Meanwhile, Dan does some digging of his own and uncovers Rufus and Lily's secret, putting him in an awkward position. | | Guest Stars: Matt Doyle as Jonathan, Dreama Walker as Hazel, Amanda Setton as Penelope, Nicole Fiscella as Isabel Coates, Yin Chang as Nelly Yuki, Connor Paolo as Eric van der Woodsen, Desmond Harrington as Jack Bass | Director: Tricia Brock
Writer: Amanda Lasher | | Songs: Franz Ferdinand -- No You Girls, Mirror Error -- The Faint, Greycoats -- Watchman, What Is Left of the Night?, Greycoats -- Watchman, What is Left of the Night? | | | |
| 34 :02x16 - You’ve Got Yale! (Jan/19/2009) | | The students are stressed out as they find out who was accepted and who didn't make the cut for early admission to Yale. Meanwhile, Serena bonds with Rachel, her Shakespeare teacher, who is unaware of what Blair has in store for her following receiving her first B; Chuck finds an unlikely ally in his feud wtih Jack; and Nate and Vanessa have a romantic evening together. | | Guest Stars: Dreama Walker as Hazel, Zuzanna Szadkowski as Dorota, Amanda Setton as Penelope, Nicole Fiscella as Isabel Coates, Yin Chang as Nelly Yuki, John Shea (1) as Harold Waldorf, Jan Maxwell as Headmistress Queller, William Abadie as Roman, Connor Paolo as Eric van der Woodsen, Desmond Harrington as Jack Bass, Laura Breckenridge as Rachel Carr | Director: Janice Cooke (1)
Writer: Joshua Safran | | Songs: Cold War Kids -- Against Privacy, Cold War Kids -- Mexican Dogs, We Fell To Earth -- The Double | | | |
| 35 :02x17 - Carnal Knowledge (Feb/02/2009) | | To get back at her teacher, Rachel, Blair puts together a devious plot to take her down. When Chuck awakes to only a vague idea of what happened the night before, Nate and Vanessa try to help him fill in the gaps of what turns out to be an intriguing mystery. | | Guest Stars: Dreama Walker as Hazel, Zuzanna Szadkowski as Dorota, John Shea (1) as Harold Waldorf, Amanda Setton as Penelope, Nicole Fiscella as Isabel Coates, Yin Chang as Nelly Yuki, Jan Maxwell as Headmistress Queller, Kate French (1) as Elle, Laura Breckenridge as Rachel Carr | Director: Liz Allen
Writer: Alexandra McNally, Lenn K. Rosenfeld | | | |
| 36 :02x18 - The Age of Dissonance (Mar/16/2009) | | Constance Billard and the St. Jude seniors put on a production of "The Age of Innocence" only to find their lives are similar to the plot of the play. During the production, Serena begins to fall for the director, Julian, and asks Vanessa for help in getting him to notice her. Meanwhile, Blair receives news that sends her on a witch-hunt; Dan and Rachel agree to part ways, but find it hard to do so; and Chuck asks his nemesis, Carter Baizen, for help. | | Guest Stars: Kate French (1) as Elle, Amanda Setton as Penelope, Nicole Fiscella as Isabel Coates, Yin Chang as Nelly Yuki, Jan Maxwell as Headmistress Queller, Zuzanna Szadkowski as Dorota, Sebastian Stan as Carter Baizen, Harmon Walsh as Julian, Laura Breckenridge as Rachel Carr | Director: Norman Buckley
Writer: Jessica Queller | | | |
| 37 :02x19 - The Grandfather (Mar/23/2009) | | Devastated by the turn her life has taken, Blair opts for a wild lifestyle instead of her perfect Waldorf life causing Chuck and Serena to become concerned. Vanessa tries to convince Nate that he needs to move on after his mother's family, The Vanderbilts, abandoned him and his mother. Trying to be honest with each other, Lily and Rufus both put together their lists of past relationships. | | Guest Stars: Aaron Tveit as Tripp Vanderbilt, Zuzanna Szadkowski as Dorota, Holley Fain as Maureen Vanderbilt, Jill Flint as Bex Simon, Sebastian Stan as Carter Baizen, James Naughton as William Vanderbilt | Director: J. Miller Tobin
Writer: Robert Hull, Etan Frankel | | Songs: MGMT -- Kids | | | |
| 38 :02x20 - Remains of the J (Mar/30/2009) | | Serena throws Jenny a sixteenth birthday party, but things spin out of control when Poppy Lifton turns the party into the social event of the season. Vanessa agrees to help Chuck in a plan concerning Blair and Nate. Meanwhile, Rufus searches for a way to cover Dan's tuition when he learns he will not receive financial aid to go to Yale. | | Guest Stars: Patrick McMullan as Himself, Dreama Walker as Hazel, Zuzanna Szadkowski as Dorota, Amanda Setton as Penelope, Nicole Fiscella as Isabel Coates, Matt Doyle as Jonathan, Yin Chang as Nelly Yuki, Connor Paolo as Eric van der Woodsen, Armie Hammer as Gabriel Edwards, Tamara Feldman as Poppy Lifton | Director: Allison Liddi
Writer: Sarah Frank-Meltzer | | | | | | | | | | | | |
| 42 :02x24 - Valley Girls (May/11/2009) | | In a flashback to the 1980s, then 17-year-old Lily Rhodes heads to Los Angeles to reconnect with her parents after getting kicked out of boarding school. Meanwhile in present day, Blair and Nate go to their senior prom together, but Chuck ensures the night does not go as planned. | | Special Guest Stars: Andrew McCarthy (1) as Richard Rhodes (80s flashback), Krysten Ritter as Carol Rhodes (80s flashback), Brittany Snow as Lily Rhodes (80s flashback), | Guest Stars: Dreama Walker as Hazel, Zuzanna Szadkowski as Dorota, Amanda Setton as Penelope, Abby Pivaronas as Veronica (80s flashback), Nicole Fiscella as Isabel Coates, Yin Chang as Nelly Yuki, Connor Paolo as Eric van der Woodsen, Caroline Lagerfelt as Celia 'CeCe' Rhodes, Cynthia Watros as Celia 'Cece' Rhodes (80s flashback), No Doubt as Snowed Out (80s flashback), Matt Barr as Keith van der Woodsen (80s flashback), Shiloh Fernandez as Owen Campos (80s flashback), Ryan Hansen (1) as Shep (80s flashback) | Director: Mark Piznarski
Writer: Josh Schwartz, Stephanie Savage | | | |
| 43 :02x25 - The Goodbye Gossip Girl (May/18/2009) | | When Gossip Girl sends out an e-mail during graduation, Serena must come up with a plan of attack. Meanwhile, The Mean Girls challenge Jenny to be Blair's successor as Queen Bee, and Lily and Rufus work to repair their relationship. | | Guest Stars: Matt Doyle as Jonathan, Wallace Shawn as Cyrus Rose, Margaret Colin as Eleanor Waldorf, Connor Paolo as Eric van der Woodsen, Michelle Trachtenberg as Georgina Sparks, Dreama Walker as Hazel, Amanda Setton as Penelope, Nicole Fiscella as Isabel Coates, Yin Chang as Nelly Yuki, Sebastian Stan as Carter Baizen, Christopher Riggi as Scott Rosson (as Chris Riggi), James Naughton as William Vanderbilt | Director: Norman Buckley
Writer: Joshua Safran | | | |
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