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The second season of the television series Gossip Girl commenced airing in the United States on September 1, 2008, concluded on May 25, 2009, and consisted of 25 episodes. It tells the story of Serena van der Woodsen and Blair Waldorf's senior year of high school in the Upper East Side, while being watched by gossip website "Gossip Girl".

The second season of Gossip Girl aired in the US on Mondays at 8:00 p.m. on The CW, a terrestrial television network. All episodes aired on CTV Television Network one day prior to their US airdate. The season was released on DVD as a seven disc boxed set under the title of Gossip Girl: The Complete Second Season on August 18, 2009 by Warner Bros. Home Video. Episodes became available to purchase to registered users of the US iTunes Store following their original airing.

Crew
The season was produced by Warner Bros. Television, Alloy Entertainment and College Hill Pictures The executive producers were creators Josh Schwartz and Stephanie Savage with Bob Levy and Leslie Morgenstein. K.J. Steinberg and Felicia D. Henderson served as co-executive producers. Producers include Joe Lazarov and Jessica Queller. The season was produced by Amy Kaufman. Jonathan C. Brody served as co-producer with Joshua Safran as consulting producer.

The staff writers were Schwartz, Savage, Felicia D. Henderson, Joshua Safran, Lenn K. Rosenfeld, Jessica Queller, K.J. Steinberg and Paul Sciarrotta. The regular directors throughout the season were Mark Piznarski, J. Miller Tobin, Patrick Norris, Norman Buckley, Tony Wharmby and Michael Fields.

Cast
The initial season had nine major roles receive star billing. Blake Lively portrayed protagonist Serena van der Woodsen, a former It girl of the Upper East Side, who returns from a mysterious stay at a boarding school in Connecticut, with Kelly Rutherford playing her mother Lily, a multiple-divorced socialite. Leighton Meester played Queen Bee, Blair Waldorf, who is less than happy to see her best friend return. Penn Badgley acted as middle-class outsider Dan Humphrey, with Matthew Settle playing his father Rufas, former rock star turned art dealer, and Taylor Momsen portraying his sister, Jenny, a freshman looking to fit in with the elite crowd at Constance Billiard. Chace Crawford portrayed Blair's boyfriend Nate Archibald, who has a thing for Serena. Ed Westwick played a womanizing player and 'bad boy' Chuck Bass. Originally only a guest star, Jessica Szohr starred as Dan's childhood best friend, Vanessa Abrams. Szohr gained a contract to the main cast list in the fourteenth episode.

Kristen Bell voiced "Gossip Girl", whose gossip commentary blog is widely visited by the youths of the Upper East Side social scene. Numerous supporting characters were given expansive and recurring appearances in the progressive storyline, including Connor Paolo who portrayed Serena's brother, Eric van der Woodsen, who had been placed into a rehab center following a suicide attempt. Margaret Colin acted as Blair's mother, Eleanor Waldorf, a fashion designer. Colin took over from Florencia Lozano who played the role in the pilot episode. Michelle Trachtenberg acts as Georgina Sparks, a girl from Serena's past who returns after escaping rehab in Utah. Sam Robards and Francie Swift portrayed Nate's parents Howard and Anne Archibald. Nicole Fiscella and Nan Zhang acted as Blair's loyal sidekicks Isabel Coates and Kati Farkas. Other members of Blair's clique include Amanda Setton as Penelope Shafai and Dreama Walker as Hazel Williams.

Other guest stars in recurring roles include Zuzanna Szadkowski as Blair's maid Dorota Kishlovsky, Robert John Burke as Chuck's father and billionaire Bart Bass, Susan Misner as Rufus' estranged wife Alison Humphrey and John Shea as Blair's father Harold Waldorf, with William Abadie as his partner Roman.

Reception
Due to the show's pedigree as an adaptation of the New York Times bestselling novel series, the show was considered to be one of the more anticipated new shows of the 2007-2008 television season. An August 2007 survey by OTX, a global media research and consulting firm, placed the show on the list of top ten new shows that viewers were aware of. The pilot episode of the season gained 3.50 million viewers on its original airing, having previously been availible as a free download on the American iTunes store. As the season progressed, ratings dropped with 2.48 million viewers tuning into the second episode. The eleventh episode marked a series low with only 1.8 million viewers tuning into watch the episode. The show was moved from Wednesdays at 9:00 p.m. to its new timeslot Mondays at 8:00 p.m following the end on the 2007–2008 Writers Guild of America strike where the final five episodes of the season were aired. Ratings increased for the season finale, with 3.00 million viewers tuning into the episode. Gossip Girl's digital video recorder ratings were high, increasing the show's profitability and the show had also been in the top five of iTunes sales.

Author Cecily von Ziegesar has expressed support for the show, noting that all of her major plot points were present in the pilot. The second episode in which the characters are shown to be attening a Brunch gained some approval from New York Magazine, stating that "there's no such thing as 'lunch' on the weekends", "that kids actually do venture outside of their neighborhoods" (since The New York Palace Hotel is at Midtown Manhattan), and "saying you live in Williamsburg makes much more sense... for real-estate emotional conflict", plus the fact Rihanna is played "in every situation." Gossip Girl was designated the "Best. Show. Ever." in April 2008, by NY Magazine. Other positive reviews came from publications Variety and the Boston Globe. John Maynard of The Washington Post feel that creator Josh Schwartz "turns it up a notch" from his former series The O.C., and noted Dan (Penn Badgley) as a standout character. Tim Goodman of the San Francisco Chronicle praised the show for its use of "Gossip Girl"'s blog as a new media element noting "there's a chance to tell a story where the Greek chorus essentially has a blog."

The show has came under critasism for containing scenes too risque for its teen audience. The Parents Television Council has shown particular criticism of the series, especially with its "OMFG" ad campaign used towards the end of the season in April 2008. It also named the episode "Victor, Victrola" the worst television program of the week in which the episode originally was broadcast. The Parents Council's negative comments include it being "the most-watched show among girls 12-17 and glamorizes casual sex and drug use among teens. [And that] storylines have featured a would-be teen rapist, threesome among teens, and teenage girls having sex with adults." Scott D. Pierce of the Deseret Morning News noted that the show is milder than a lot of what's shown on MTV, but still warned parents of several scenes in the pilot. He said it includes "among other things, a teenage girl climbing on top of a boy and removing his clothes; drunken teens having sex; teens smoking pot; teens drinking in bars, in a limo and at a party; a teen boy getting amorous with a girl who fights him off; and that same teen boy essentially attempting to rape a freshman girl who is supposed to be, what, 14?".

The series has also been critasized for having less-than believable storylines and has been described as a guilty pleasure rather than an hour's worth of must-watch television.

Episodes
"Series #" refers to the episode's number in the overall series, whereas "Episode #" refers to the episode's number in this particular season. The original airdate and amount of viewers refer to the episodes broadcast on The CW.

DVD release
The DVD release of season two was released by Warner Bros. in the US on August 18, 2009, after it had completed broadcast on television. As well as every episode from the season, the DVD release features bonus material including a downloadable audiobook, deleted scenes and behind-the-scenes featurettes.