List of Gossip Girl characters

This article contains character information for the American teen drama, Gossip Girl. The series is based on the popular book series of the same name written by Cecily von Ziegesar. Featuring an ensemble cast, the series begins by introducing Serena van der Woodsen (Blake Lively) and her best friend Blair Waldorf (Leighton Meester), wealthy playboy Chuck Bass (Ed Westwick), Chuck's best friend, Nate Archibald (Chace Crawford), freshman Jenny Humphrey (Taylor Momsen), Jenny's brother, Dan Humphrey (Penn Badgley), and Dan's best friend and lover, Vanessa Abrams (Jessica Szohr), all of whom reside in the Upper East Side of Manhattan. Other main characters are Lily Humphrey (Kelly Rutherford), a socialite, mother to Serena and wife to Rufus Humphrey (Matthew Settle) a former rock star, father to Dan and Jenny and husband of Lily. The series is narrated by a seemingly omniscient character, "Gossip Girl" (voiced by Kristen Bell).

Main characters

Serena van der Woodsen

Further information: [[:Serena van der Woodsen]]

Portrayed by Blake Lively since the pilot, Serena van der Woodsen is the it girl of the Upper East Side and best friend of Blair Waldorf. Recently returned from a Connecticut boarding school for reasons unknown to her friends, as was her departure from Manhattan a year prior to the show's beginning. Serena van der Woodsen comes across as down-to-earth for someone from the UES, but things, relationships (Dan, Nate) and opportunities (fashion shoots) seemed to be handed to her on a silver platter. Serena's past as the partying and whoring as 'it girl' causes her to leave Manhattan for mysterious reasons. Even more mysterious, she abruptly returns to the high society world of Manhattan. She is described as being breathtakingly beautiful and tall with blonde hair. During the first season, she deals with a spiteful Blair, her incident with Nate and a new relationship with Dan. Her relationship with Dan first faces the return of his best friend, Vanessa's and her gradual warming up to her, Dan's acceptance of herself and the high society world she lives in. Their relationship ends during her mother's wedding to Bart Bass due to her frenemy Georgina making life horrible for her and her friends. The second season has Dan and Serena renewing their relationship but facing the reality that they could never be together, Dan's incident with a new girl and a scandal with a teacher, their residual feelings for each other and the discovery of their parents' love child. This season also sees Serena's mother, Lily, adopting Chuck Bass, thus making the two of them step-siblings. Serena leaves Manhattan during the summer and returns in the third season a local celebrity. She was with Nate but wanted a break.Serena went to Paris with her friend Blair trying to figure out if she wants to be with Nate,or Dan. When she got back they both were with other people. Serena decides to go to Columbia.

Blair Waldorf

Further information: [[:Blair Waldorf]]

Portrayed by Leighton Meester since the pilot, Blair Cornelia Waldorf is the queen bee of the social scene of Manhattan and Constance Billard High School. An only child, she is introduced as the daughter of a divorced fashion designer mother and a homosexual father and the longtime girlfriend of Nate Archibald although she also fell for and is dating Nate's best friend Chuck Bass. Blair is often portrayed as haughty, shallow, intelligent, and scheming. Despite her uptight, frivolous nature, she "works for everything she's ever gotten", in contrast to Serena, and despite her snobbish ways, she is a good friend and constantly looks out for those she cares about. She is described as a stunning and beautiful brunette of medium height. Blair faces her crumbling relationship with Nate and a new relationship with Chuck in the first season and her return to power as Queen Bee after a power struggle with Jenny Humphrey. Chuck leaves her alone in the summer that gives her time to return in a short relationship with a British noble during the second season. Her relationship with Chuck changes as he tries to win her back and she tries to own up to her own feelings towards him, Blair becomes tired of the high school pettiness until the her admission to Yale is compromised. Her loss of Yale places herself in a new life. She resumes her relationship with Nate but eventually ends it. By the end of the second season she and Chuck embark on a relationship. The third season has Blair adjusting to her new life in NYU and her continuing relationship with Chuck. At the end of season three Blair leaves Chuck and goes to Paris with Serena. When Chuck comes back they have a series of wars but end them when they make a peace treaty. They break that peace treaty by having sex.

Dan Humphrey

Further information: [[:Dan Humphrey]]

Portrayed by Penn Badgley since the pilot, Daniel Rudolph "Dan" Humphrey is a loner. He is the son of a rock musician turned art gallery owner, Rufus Humphrey, his absentee mother Allison Humphrey, and the elder brother of Jenny Humphrey. He first meets Serena van der Woodsen at a party where she seemed to be the only person who spoke to Dan when she greeted him. Smitten with Serena, he finds himself immersed in her moon-eyed world where he is made to attend St. Jude's at his father's bidding. Dan is an aspiring writer who dedicates his first poem to Serena and later becomes an assistant to a popular writer. He initially dreamed of attending college at Dartmouth, but decided to pursue Yale, believing it to have the better English faculty. His recent break up with Serena eventually changes his luck with women but still has feelings for her that leads to Serena breaking up with Aaron and the two returning to a new relationship until news of a love child between their parents makes the road quite rocky for them. He then becomes involved in a scandal with a teacher named Rachel Carr and the scandal leads to the two ending their relationship for the final time. He now attends NYU after losing his money to a scheme involving Poppy Lifton and Serena's new love interest, Gabriel Edwards. With Rufus and Lily's relationship now turning to marriage, Dan has adapted to his families' new wealthy lifestyle. Dan has becomes a well-known face amongst the freshman in NYU unlike Blair who becomes a social pariah and starts dating Olivia Burke, a Hollywood actress. The two break up when Olivia sees that Dan and Vanessa have feelings for each other.

Nate Archibald

Further information: [[:Nate Archibald]]

Portrayed by Chace Crawford since the pilot, Nathaniel "Nate" Archibald is torn between Serena and Blair – both of whom he has romantic histories with, the so-called golden boy also frequently finds himself making life decisions. His closest friend is Chuck Bass. After his relationship with Blair ultimately falls apart, he has a fling with Vanessa Abrams. When his father must flee New York to escape the FBI, Nate enters a relationship with an older married woman, Duchess Catherine Mason Beaton. The relationship turns into an arrangement of sex for money when the Archibalds' accounts become frozen. His frozen accounts result in him temporarily moving in with the Humphreys. He briefly has a crush on Jenny, but it never turned out to be anything serious. In the second season, he pursues a relationship with Vanessa but when Nate gets in touch with his Grandfather again, their relationship declines and he breaks up with Vanessa because of Blair in the end. They eventually break up and he goes on a trip to Europe for the summer. He returns in the third season in a Romeo and Juliet relationship with Bree Buckley but ends up being used for Bree to get her revenge on Carter Baizen, thus ending their relationship during Lily and Rufus' wedding.

Jenny Humphrey

Further information: [[:Jenny Humphrey]]

Portrayed by Taylor Momsen since the pilot, Jennifer Tallulah "Jenny" Humphrey is introduced as a freshman at Constance Billiard with a desire to carve her own place in the in-crowd, Jenny is impressionable and quickly becomes the pawn of several characters. She, amongst other girls, harbors a crush for Nate Archibald. She also has a tight-knit relationship with her brother, Dan, which proves handy as she finds herself in frequent need of help due to her bad judgment. Jenny dreams of becoming a designer, her efforts eventually pay off after receiving a letter of internship at Eleanor Waldorf's studio. When Jenny begins to feel that Eleanor is exploiting her talent, she teams up with a bad girl model Agnes to jump-start her own line, J Humphrey Designs, to disastrous consequences. She returns to Constance and slowly transitions to become her own person. By the end of the second season, she is crowned the new Queen Bee. In the third season, Jenny's position as queen begins eroding her friendship with Eric and her own personality. She then hooks up with a drug dealer and tried to lose her virginity with him, but stopped just in time. At the end of season three she ends up losing her virginity to Chuck. She was then shipped off to live with her mother.

Chuck Bass

Further information: [[:Chuck Bass]]

Portrayed by Ed Westwick since the pilot, Charles Bartholomew "Chuck" Bass is a cynical, world-weary, handsome and suave, Chuck has no qualms about living life on the edge. The childhood best friend of Nate, his reputation of womanizing and a patron of baser habits make them complete opposites. He is the only son of Bart Bass, and his mother is thought to be deceased (died in childbirth). Portrayed firstly as the 'bad boy' of the group, Chuck demonstrates a nicer side in the succeeding episodes when he lends Nate $10,000 to get out of a shady poker game, falls in love with Blair, and acts as a surprisingly supportive stepbrother to Serena and her brother Eric. He and Blair finally become a couple towards the end of the first season, yet Chuck's insecurities and fear to let anyone close cause him to leave Blair waiting at the helipad on their supposed trip to Europe. During the second season, Chuck's activities revolve mainly around winning Blair back, realizing who he is and struggling with his devious nature, the death of his father, confronting his deviant uncle Jack Bass. At the end of the second season, Chuck finally tells Blair that he loves her and the two share a romantic kiss. The third season starts with Chuck and Blair playing games to keep their relationship interesting. Chuck then begins a new mission of making a name for himself and getting out of his father's corporate shadow. He finds his real biological mother, but is doubtful about her at first. She turns out to really be his mother, but lies and says she is not after she betrays him by being involved in a plot with his scheming uncle, Jack Bass, the details of which involve filing a lawsuit against Chuck and taking away the ownership of his hotel. He makes a deal with Jack for him to have his hotel then he could have Blair, She heard about this and was willing but Jack would not. After Chuck and Blair break up he sleeps with Jenny Humphrey. Thuse, giving them no hope of getting back together. Chuck is so sad about Blair, he goes to an unknown place and goes into an alleyway. Two guys take his stuff(including the ring he was going to give to Blair) and shoot him. He is taken care of by a lady named Eva. When he comes back, he starts a sexual relationship with Blair. (for more information, look at Blair Waldorf).

Vanessa Abrams

Further information: [[:Vanessa Abrams]]

Portrayed by Jessica Szohr since season one, being a recurring character in episodes 6 till 12 and a main character since episode 14, Vanessa Marigold Abrams is the childhood best friend of Dan Humphrey. Prior to Dan's relationship with Serena, she and Dan were inseparable, and the two developed a mutual attraction that was dashed when she moved to Vermont. A year later, she returned to move in with her big sister, just as Dan was trying to make things work out with Serena. Despite her continued attraction to Dan, she backed off when she saw that Dan genuinely loved Serena. Later, she strikes up a relationship with Nate Archibald but they break up before the summer and resume by the time it's over. Unlike most of the cast, Vanessa is home-schooled, and thus has the free time to man a café she added to Rufus's art gallery during his summer absence. After many complications with Nate, ranging from his summer fling with Catherine Mason and subsequent troubles, his sudden relationship with Jenny and his return to the Vanderbilt family circle, their relationship ends when Nate and Blair get back together. Nate's one-time favor of her applying to college has led her to attend NYU. Vanessa then embarks on a relationship with Scott Ronsson that ends when she is forced to let him go because of the damage it could do to Rufus and Lily's relationship.

Lily Humphrey

Portrayed by Kelly Rutherford since the pilot, Lily Humphrey, born Rhodes, previously Bass and van der Woodsen, is the multiple-divorced, ex-ballerina, and socialite mother of Serena and Eric van der Woodsen, Lillian has a colored history as a former groupie of Dan and Jenny's father, Rufus, that she would rather not acknowledge. Her previous marriage before Rufus Humphrey was to Bart Bass. Despite her constant concern for appearances and status in high society, it can be assumed that she lived as indulgently as Serena during her wild child years. Her similarity to Serena can especially be seen when she cries and is unable to make any decisions, both of which are behaviors commonly seen in Serena. It is revealed she was also institutionalized at 19 much like her son Eric. It was later revealed that it was not because of a suicide attempt, but because she was pregnant with Rufus's child. Rufus and Lily returned to New York, and became a couple. The character is portrayed by Brittany Snow in flashback sequences. She adopts Chuck Bass in the second season. In the last episode of the second season, Lily and Rufus became engaged and married in the fifth episode of the third season. In season 4, Lily becomes a "grandmother" from Georgina and Dan. Dan and Georgina name the baby Milo Humphrey. It was revealed that Lily had put Ben Donovan in jail for having an "affair" with Serena, which was the current rumor at Serena's school in Connecticut. As reveled in the flashback sequences, her father was a music producer, she was raised in Montecito, California and that her birthday is August 7, 1967.

Rufus Humphrey

Portrayed by Matthew Settle since the pilot, Rufus Humphrey is a former rock star whose marriage has fallen apart, he is also an owner of a fledging art gallery. Determined to give his children a quality education, he enrolled them at private day schools which lead him to bump heads more than once with his former flame, Lillian van der Woodsen. He got a divorce from his wife, Alison Humphrey who was having an affair with a man named Alex. He has difficulty, as a single parent, managing his growing children, in particular the strong-willed Jenny, and often enlists Lily's aid. Although he and Lily attempted to rekindle their old relationship prior to Lily's marriage, she ultimate chose to remain friends with Rufus and to marry Bart Bass. After Bart's death, the pair rekindle their romance when they search for their son. In the last episode of season 2 Lily and Rufus became engaged and married in the fifth episode of season 3. In season 4, Rufus doesn't believe Georgina, when she says that she and Dan have a son, Milo Humphrey. In the season 4: “Double Identity” episode, Rufus finds Milo’s ID bracelet, which says that Milo has a different blood type than Dan.

Gossip Girl

Voiced by Kristen Bell since the pilot, "Gossip Girl" is the narrator of the show, an unseen character whose gossip commentary blog is widely visited by the youths of the Upper East Sid social scene, often stirring the lives of the main characters. Her (or his) identity remains a secret but still manages to lure readers with catty wordplay and scandalous news provided via tips through the members of the Upper East Side social network. Gossip Girl has avoided discovery twice when her blog was the subject of getting shut down during Dan's incident with Miss Carr and when Serena attempted to confront her personally but failed. Gossip Girl showed a personality trait in the fourth season episode 'The Townie' where she responded to a request from Blair for the location of Juliet with the address and 'Go get the bitch.' showing that she does not appreciate anyone who may threaten the validity of her blog, leading one to believe she may be personally motivated.

Recurring characters

Eric van der Woodsen

Portrayed by Connor Paolo since the pilot, Eric van der Woodsen is the troubled younger brother of Serena and heir to the Van Der Woodsen fortune, his suicide attempt becomes the catalyst for Serena's homecoming. Revealed his homosexuality later on in season one to everyone, after his boyfriend Asher pretends to have a relationship with Jenny Humphrey. His friendship with Jenny is repaired after she apologizes in the beginning of the second season. They soon become best friends through the second season. This once again falls apart during Season 3 after Jenny accepts her role as Queen Bee but soon, Eric makes amends with her after Serena's accident. He then begins to date Jonathan Whitney but their relationship falls apart due to Eric's once obsessive need to "teach Jenny a lesson". In the next season, he begins dating a bisexual named Elliot.

Dorota Kishlovsky

Portrayed by Zuzanna Szadkowki since the pilot, Dorota Kishlovsky is the Waldorf's Polish housekeeper and who cares deeply for Blair. Despite often snapping at her in numerous episodes, Blair is shown to see Doroda as a stand in mother figure. In the web-series "Chasing Dorota", it is revealed that Dorota is actually a Polish countess with a secret husband, Stanisław. She fled to America to flee her family and began working for the Waldorf family in 2004. She eventually divorces her husband and is currently engaged to Vanya, the Russian doorman at the van der Woodsens' apartment building. In "The Treasure of Serena Madre" she is revealed to be pregnant with Vanya's child and in "The Unblairable Lightness of Being" she and Vanya get married. She gives birth to a daughter (Anastasia) in the season finale, and she and Vanya move into an apartment in Queens, bought for them by Cyrus.

Eleanor Waldorf

Portrayed by Florencia Lozano in the pilot and Margaret Colin since episode episode four, Eleanor Waldorf-Rose is the impassive, fashion designer mother of Blair Waldorf. Her decades-long marriage to Blair's father, Harold Waldorf, ended when Harold left her to pursue a relationship with a French male model, Roman. It is implied through flashbacks that Eleanor knew about Harold's bisexuality. Her clothing line 'Eleanor Waldorf Designs' is being distributed by Barney's and Bendel's. She also has a rivalry with Marc Jacobs and once employed Jenny as an overworked intern. Her relationship with Blair is strained, but Jenny tells Blair that Eleanor loves Blair "in her own way".

Howard Archibald

Portrayed by Sam Robards in seasons one, two and four, Howard "The Captain" Archibald is the father of Nate Archibald. Howard is a white-collar criminal and a recovering cocaine addict. He leaves to escape arrest, still addicted to cocaine and Nate punches his father before the Captain could get into his limo and fled to Dominica. In the second season, when he returned to New York, to take Nate and his mother with him, Nate gave him a choice. Either go back to Dominica and never speak to his family again or turn himself in to the police. Howard decided to do the right thing and chose to turn himself in. In the fourth season, Howard later receives a file for divorce while in jail, a few months before his release from prison. When he is paroled, Howard soon takes a job with Russell Thorpe.

Isabel Coates

Portrayed by Nicole Fiscella in seasons one and two, Isabel Coates is Blair's loyal sidekick, who remains her friend despite her losing rank as Queen Bee. She was best friends with Kati Farkas and tends to match outfits with her. During the first season, she and Kati often appeared in Blair's Audrey Hepburn dreamscapes and at one point she and Kati also appear in Dan's dreams. She is also concert pianist. Isabel and Penelope contribute to the new rift between Blair and Serena when the position of Queen shifts from Blair to Serena. Her see-through dress that she intended to wear to the Snowflake Ball is used to humiliate Vanessa. Isabel, Penelope and Hazel are all present when they plan on declaring Emma Boardman as the new Queen, which went to Jenny. Both Isabel and Penelope refuse to have a girl from Brooklyn carry out their legacy but Blair convinces them otherwise.

Kati Farkas

Portrayed by Nan Zhang in season one, Kati Farkas is Blair's loyal sidekick until she loses her rank as Queen Bee. She was best friends with Isabel Coates and regularly matches outfits with her. During the first season, she and Isabel often appeared in Blair's Audrey Hepburn dreamscapes and at one point she and Isabel also appear in Dan's dreams. Kati's brother owns the apartment that would be the setting place for Blair's Japanese-themed seventeenth birthday, which led to Blair and Chuck's continuing secret relationship during the first season. Her parents move her back to Israel after spring break.

Bart Bass

Portrayed by Robert John Burke in seasons one and two, Bartholomew "Bart" Bass, is Chuck's billionaire father, founder of Bass Industries and was married to Lily van der Woodsen. His family lived at the New York Palace Hotel, which he owned. His money was self-made, as opposed to inherited like most Upper East Side families. He was controlling with his family, ruthless in business and demonstrated little to no interest in Chuck's life. In season 2, with Dan's help, he and Chuck try to mend their relationship, but he suddenly dies in a limo accident. In season 3, he reappears as a ghost on the anniversary of his death.

Carter Baizen

Portrayed by Sebastian Stan in seasons one, two and three, Carter Baizen is a St. Jude's graduate and rival of Nate and Chuck. It is mentioned that he turned his back on his parents and so was left without a trust fund and was forced to take matters into his own hands by shaping his own future, something that Nate desperately wants. Nate idolizes him at first until Carter tries to extort money from him in a rigged poker game. He later becomes Serena's escort to the cotillion and is thwarted by Nate's punch after Chuck manipulates Nate into thinking that Carter is pursuing Blair. CeCe had called Carter a week before the cotillion and reveals this to Serena, whose opinion of her grandmother changes. In the 2nd season, Carter resurfaces in New York with the mysterious Elle but ends up being involved with Blair and sleeps with her, contributing to her downward spiral. He soon leaves New York as Serena and Chuck intervene. In the 2nd season finale, Carter returns to New York to tell Serena that he has found her father. During the premiere of season three, it is discovered that he and Serena spent their summer in Europe in pursuit of her father. In light of Serena's failure to capture her father's attention, Carter reveals his feelings to Serena and they share a kiss. Their relationship ends when it is revealed that he left Bree Buckley at the altar, earning the wrath of the Buckleys as Bree has her cousins called in during Rufus and Lily's wedding to bring Carter to Texas to work at an oil mill to pay off his debt. Serena then gambles on a high stakes poker game for Carter's freedom and fails. She then takes matters into her own hands and has him freed but Carter refuses to resume their relationship, saying that he would have preferred it if Serena didn't save him so that he could make amends and leaves. Carter resumes his habit of lying when he informs Serena of her father's definite location. Serena's disappears with him, which creates a strain in her relationship with Nate. Serena later finds out that he had known about where her father was since before they began dating, but had been delaying the information from her in order to get closer to her. She then forces him out of the limo.

Anne Archibald

Portrayed by Francie Swift in seasons one, two and four, Anne Archibald, née van der Bilt, is the mother of Nate Archibald. During the events of the first season, she aids her husband in dealing with Eleanor Waldorf's accounts. She once promised to Eleanor Waldorf to give Blair her Cornelius Vanderbilt engagement ring should Nate and Blair ever be engaged but when Blair witnesses Nate's troubles with his father she ends the relationship. By the second season, Nate's mother whose financial assets have been frozen since her husband's guilty departure have caught up with her and their house in Manhattan is seized, leaving Nate to lodge in temporarily with the Humphreys. Anne Archibald's reputation was also in danger during her financial situation with Chuck giving her loan after selling his club, Victrola but this causes Nate to end his friendship with Chuck. Her financial troubles come to an end when Nate convinces his father to come clean to the FBI and she sheds tears for the arrest of her husband. A short while before her husband is released from prison however she files for divorce.

CeCe Rhodes

Portrayed by Caroline Lagerfelt in seasons one, two and three, Celia "CeCe" Rhodes is Lily's mother and Serena's grandmother. She lives in Santa Barbara, California and visits Lily and Serena in New York City a few times every year. She is portrayed as a very wealthy, highly conservative, uptight, indimidating, snobbish, and impassive socialite who looks down and scorns at all people whom are of middle or lower classes. She caused the breakup of Rufus and Lily back in the day by making Lily choose between her family inheritance and Rufus. Intimidated, Lily chose her inheritance. CeCe also tried to break up Serena and Dan to no avail by inviting Carter Baizen (who comes from a wealthy family) to the cotillion. During the first season, CeCe manipulated her daughter and granddaughter by declaring that she had a terminal illness, claiming that the doctors found 'something' in her lungs. Although she later admitted that this was a lie to gain sympathy, she was later seen taking pills. Her cold and manipulative personality changes in the second season when she lets Dan into the White party by making him her escort, seeing that he still has feelings for Serena. After Bart Bass' funeral, she reveals the reason why Lily was in a sanatorium. During the events of Serena's arrest, Lily and CeCe resume their mother-daughter fight but later patch up their problems before CeCe leaves. CeCe's supposed sudden illness in the third season causes Lily to leave Manhattan to take care of her in California for a couple of months, with CeCe returning for an appearance on the Thanksgiving episode.

Penelope Shafai

Portrayed by Amanda Setton in seasons one, two and four, Penelope Shafai is a member of Blair's clique until she was dethroned as queen bee; constantly shifts her allegiance between Blair and Jenny. She makes no secret of her crush on Nate when she aids in Blair's dethroning and Jenny's ascent as Queen with Jenny earning her and Hazel's favor when Jenny salvages herself after Blair attempted to sabotage her birthday. She helps host Jenny's party with Asher and gives the freshman the benefit of the doubt when she lied about having sex with Asher Hornsby, eventually ending her friendship with her when Jenny reveals the truth. She is also a national Merit Scholar. Chuck persuades her to ruin Amanda Lasher's hair which ends up in a fight between Dan and Serena. Isabel and Penelope contribute to the new rift between Blair and Serena when the position of Queen shifts from Blair to Serena. Penelope attempts to get Nate as her date to the Snowflake Ball, planning with the girls and a reluctant Jenny to humiliate Vanessa. Isabel, Penelope and Hazel are all present when they plan on declaring Emma Boardman as the new Queen, which went to Jenny. Penelope refuses to have a girl from Brooklyn carry out their legacy but Blair convinces them otherwise. Penelope returns in season 4 as she attends Columbia University. She is currently a member of an exclusive club, the Hamilton House, and continues her rivalry with Blair and Serena.

Hazel Williams

Portrayed by Dreama Walker in seasons one and two, Hazel Williams is a member of Blair's clique until she was dethroned as queen bee; constantly shifts her allegiance between Blair and Jenny. Jenny steals her mother's Valentino dress during Jenny's birthday. She forgives her right after Jenny impresses Blair's clique by bringing Nate during their dinner at Butter. Like Penelope, she gives Jenny the benefit of the doubt when Jenny lies about having sex with Asher, eventually breaking her friendship with Jenny. Along with Isabel and Penelope, she succeeds in publicly humiliating Vanessa at the Snowflake Ball. Hazel has tendency to be desperate for a boyfriend and Jenny at one point blackmails her to treat Nelly Yuki better by reminding her that she once hooked up with her cousin. She also regularly checks Gossip Girl's blog and once suffered symptoms of withdrawal when Rachel Carr has cellphones banned from Constance premises. Isabel, Penelope and Hazel are all present when they plan on declaring Emma Boardman as the new Queen.

Georgina Sparks

Portrayed by Michelle Trachtenberg in seasons one till four, Georgina Sparks is a girl from Serena's past who returns after escaping rehab in Utah. Before that, she was supposed to be at an Equestrian circuit but sold her show pony for cocaine, prompting her parents to send her to rehab. Her sudden return causes Serena to relapse to her old habits and even fixes Serena's drink which causes to wake up late for her SATs. After Serena asks that she leave Manhattan but Georgina refuses, blackmailing Serena and now determined to ruin her life. Georgina nearly persuades Dan to sleep with her but this leads to a confrontation with Serena. Blair, taking matters into her own hands informs her parents of her location, persuades Dan to make Georgina fall for Blair's trap and is sent to a reform school recommended by Blair herself. She reappears late in the 2nd season where Georgina is at a church camp and appears to be a completely reformed "saved" Christian. That is, until Blair persuades her to help them in a plot to take down Poppy. After which, Georgina went back to her old scheming ways. At the end of the 2nd season, she is about to attend NYU and requests Blair as her roommate. She reappears in the 3rd season and surprises Blair Waldorf when she shows up as her lovely roommate. After her relationship with Dan is once again thwarted, followed by blackmailing Vanessa and ruining Rufus and Lily's wedding, she gets tricked and sent away with a Russian prince, a plan to get rid of her set by Blair and with the assistance of Dorota. After a long absence, she returns from Belarus wearing a blonde wig and large coat, desperately seeking the help of various Upper-East Siders with her "problem." It is revealed that Georgina is pregnant with what she says is Dan's child. A son that they named Milo. She runs off again, leaving Dan with their son but it is later revealed that he is not the father, just another one of Georgina's schemes. Georgina takes Milo back when Dan signs the birth certificate, ending her manipulative plot and leaves Dan.

Nelly Yuki

Portrayed by Ying Chang in seasons one and two, Nelly Yuki is Blair's academics rival. She's a Merit Scholar, a Peabody Scholar and an Intel Science Talent Search Finalist. Itzhak Perlman gave her her first violin and her parents own half of Tribeca. Despite being sabotaged by Blair during the SATs, her recent break-up with her boyfriend Todd, she has become her friend and brands Jenny Humphrey a liar, ending Jenny's status as Queen Bee. Is part of Blair's clique in season two. Jenny tries to help Yuki out when she fears the girl is being bullied too much by the other clique members, using Yuki's knowledge to blackmail them into backing off. When Yuki realizes Jenny has no intention of taking over as the new Queen Bee, she reveals she was playing Jenny the whole time to take advantage of a regime change and goes back to the clique. Nelly eventually approves of Jenny becoming Queen at the end of the 2nd season.

Jonathan Whitney

Portrayed by Matt Doyle in seasons two, three and four, Jonathan Whitney is Eric's ex-boyfriend. In "The Goodbye Gossip Girl", Jonathan was mistakenly identified as "Gossip Girl" when the presiding room was silenced and someone texted her, it turns out that he had hacked Gossip Girl's website. In season 3, Jonathan was absent for a few episodes - he was with his grandparents - when he returned, he and Eric challenged Jenny's authority over the school by sitting higher on "the steps" than her and her cronies, this resulted in Eric being splattered with yogurt. That night, at a party, ("They Shoot Humphreys, Don't They?") Jonathan is egged by Jenny's cronies, angering Eric, who plots to ruin Jenny's Cotillion. But when Jonathan learns of Eric's scheming with Blair, he breaks up with him. In season 4, Jonathan tries to reconcile with Eric.

Aaron Rose

Portrayed by John Patrick Amedori in season two, Aaron Rose is an artist Serena met at Rufus' art gallery. He has recently met Serena at summer camp in Europe many years ago, were somewhat "married" and moved on. He reminded Serena that they have met before by asking the fate of Cecil, the Caterpillar. Aaron is somewhat of a romantic and impresses Serena by taking pictures of her, renting a billboard in Times Square to "introduce his favorite his places to her.", but Serena distances herself from him when she discovers that he likes dating multiple women at once. Aaron eventually steps up and makes his relationship with Serena exclusive. When Aaron discovers Serena's colorful past but accepts it when he tells her that he's a recovering alcoholic. He is Cyrus' son and becomes Blair's stepbrother on Cyrus and Eleanor's wedding. After going to Buenos Aires for Christmas with Serena, the two end their relationship because of Serena's residual feelings for Dan. Blair references Aaron and his art during a party in Brooklyn in the 3rd season.

Cyrus Rose

Portrayed by Wallace Shawn in seasons two and three, Cyrus Rose is Eleanor Waldorf's divorce attorney and an entertainment lawyer, who becomes her new love interest in season 2. Cyrus is also the father of Aaron Rose, from a previous marriage. Blair is excited to meet him at first, as she believes her mother to have the best taste in men. She is shocked to find that he is old, bald 5 feet tall, with a crude, jolly personality, and is a 'hugger'. Blair describes meeting him as "expecting Cary Grant and getting Danny DeVito" He also has a catchphrase, "Not enough!", once using the catchphrase to comment on Blair's pumpkin pie during Thanksgiving, and on hugs and other occasions. During Blair's eighteenth birthday, she and Cyrus have a conversation about Mei Li, the 'golden lion', a Vietnamese woman he met during the Vietnam war that leads him to divorce his first wife. When Mei Li died during the Vietnam war, he didn't find love until he met Eleanor Waldorf. Blair uses this knowledge to separate to Cyrus from Eleanor but Cyrus uses the arrival of Cindy Lauper to prey on Blair's guilt causing Blair to admit her mistake and slowly accept Cyrus. The two return to her eighteenth party to convince Eleanor to take him back. They get married the day after and announce the engagement during Thanksgiving, bringing his jolly family with him that irritates Blair. Cyrus and Eleanor get married during the 2nd season. Cyrus returns in the 3rd season and convinces Dorota to get married, buying her and Vanya an apartment in Queens.

Jack Bass

Portrayed by Desmond Harrington in seasons two and three, Jack Bass is Chuck's uncle who comes to New York upon hearing of his brother, Bart Bass' death, and slept with Blair on New Year's. Jack headed Bass Industries in Australia and served as Chuck's legal guardian when Bart died. He then plots to take Bass Industries from Chuck and sets him up by having the Board of Bass Industries to witness his debauchery and inebriation. Chuck turns to Lily to remove Jack from Bass Industries due to his incompetence at handling the assets of Bass Industries causes the business to become stagnant. Jack loses hold of Bass Industries when Lily decides to become Chuck's new legal guardian, thereby transferring a significantly large power of the company to her. Jack then confronts Lily while he is high and attempts to rape her until Chuck has him kicked out of the opera. Jack is then sent back to Sydney. By the third season, during Chuck's opening of his new hotel, Blair aids him in getting a liquor license for Chuck by contacting Jack. Chuck confronts Blair for contacting Jack and Blair receives flowers and a note stating that the liquor license is fake. Blair and Chuck eventually allow the police to end the opening party and therefore receive enough press and publicity for future clients for a genuine speakeasy that Chuck has been planning. Chuck goes to find Jack, whom could maybe help him take back Bass Industries from Lily, who is going to sale it. Jack will return in Season 4 in a February 2011 episode.

Trip van der Bilt

Portrayed by Aaron Tveit in seasons two and three, William "Trip" van der Bilt is Nate's older "political minded" cousin, who was getting married in the 2nd season and argues with Vanessa over Nate's future. He then convinces Nate to take the internship at the Mayor's office but Nate does otherwise by traveling to Europe for the summer. On the 3rd season he ran for office, with Nate's help and wins the congressional seat, no thanks to his wife's interference. Trip starts an affair with Serena when he discovers that Maureen created a plot that would win him the election. Their affair ruins his marriage and compromises his career and is discovered during a disastrous Thanksgiving. The following day, Trip and Maureen agree to certain terms concerning Serena and his career. Serena refuses to continue such an agreement of her becoming a mistress and they fight. While on the road back to Manhattan, Trip and Serena collide towards a bridge and Trip places Serena on the driver's seat to remove himself from any implication of arrest. Nate later punches him for getting Serena into an accident.

Maureen van der Bilt

Portrayed by Holley Fain in seasons two and three, Maureen van der Bilt is Tripp's diabolical wife who was getting married during the 2nd season and seemed to be normal in the eyes of William Vanderbilt. She reveals her more manipulative side on the 3rd season when she concocts a plan to have Trip win the Congressional seat left by the late Congressman Krueger. She hires someone to purposefully drown himself to be saved by Trip, giving him an advantage to win the election by giving him a heroic image. When Nate and Vanessa discover that the man in the video was hired to help Trip win the election, Nate and Trip accuse William and swear that they will avoid any association with him. William soon discovers Maureen's plot but only after Trip wins the election. Serena then earns her ire when she and Trip start and affair and are discovered by Chuck during Thanksgiving, with Nate revealing the affair to Maureen. An upset Maureen leaves early for Thanksgiving but returns for her jacket, identical to Lily's, and gets Lily's letter from her ex-husband. Maureen uses it to blackmail Serena but offers her a chance to become Trip's mistress, something she and Trip have agreed on to save his career, starting the cycle of events that would lead to Serena's car crash. She decides to keep her husband from getting into anymore trouble and silences him when he tries to justify the accident with Serena to Nate.

Vanya

Portrayed by Aaron Schwartz since season two, Vanya is Dorota's husband, father of her daughter Anastasia and doorman at Rufus and Lily's apartment.

Scott Rosson

Portrayed by Chris Riggi in seasons two and three, Scott Rosson is the biological son of Rufus and Lily, whom Lily gave up when he was born. When Rufus and Lily came looking for him 20 years later, his adoptive parents told Lily and Rufus he died in an accident. In truth it was his adoptive parent's other son who was in the accident. Afraid that Rufus and Lily would want to take him back, his adoptive parents lied so they wouldn't lose their other son. In the season finale of season 2, Scott left home to go to New York, looking for his birth parents, while his adoptive parents think he's in Portland.

Olivia Burke

Portrayed by Hillary Duff in season three, Olivia Burke is Vanessa's roommate at NYU, who is a famous movie star, trying to lead a normal college life. In season 3 she met Dan accidentally. They later started dating until she realized he had strong feelings for Vanessa. Although still choosing to be with her, Olivia leaves for a movie shoot but promises to be back in The Fall. Hilary Duff won a Teen Choice Award for her role as Olivia.

Damien Daalgard

Portrayed by Kevin Zegers in seasons three and four, Damien Daalgard is the son of the Belgian ambassador and a drug dealer. Later befriends Jenny and uses her as a drug mule and gets her to become a dealer. He begins dating Jenny and wanted to have sex with her, and when she refused he left her. Later on, Damien tries to help Blair and Dan find Juliet when he finds out that he sold Juliet a large amount of drugs such as cocaine, pills and ether which was used to drug Serena. It was revealed in "The Hurt Locket" that he was very intelligent and athletic, and also went to the same boarding school as Serena when she went away.

Juliet Sharp

Portrayed by Katie Cassidy in season four, Juliet Sharp is an intriguing woman that Nate first met in a bar while he's on a date with one of the girls of Chuck's little black book. She knows much more about the gang than what she lets on, and she's the one who advises Vanessa to get back together with Dan, so that Nate can get Serena back. At the end of the third episode, she meets a man in prison, Ben, who is later found out to be her brother. When Nate begins to suspect Juliet's strange behaviour and busy schedule, he askw her to tell him more about her life. She takes him to what appears to be her apartment, but while Nate goes to see the place, she hands some cash to a man who tells that the real owners of the apartment will be back in the next day. Her glamorous, impenetrable façade and dismissive approach to love actually hides a sensitive, caring nature and as the season progresses, she declares to having genuine feelings for Nate. But after her brother attacks Nate's father in jail for Juliet's attempt at forgoing their plans, she calls Nate, and ends their relationship for the sake of Howard's safety. After she hangs up, Serena's professor Colin then enters the room and hands Juliet a cheque, thus making us believe that he is in on her plan to sabotage Serena. We later learn that he is in fact her cousin, and that the cheque was to cover her rent and school fees, he has no idea of her and her brother's plans for Serena. Juliet, Vanessa, and Jenny come together to strike a savage blow against Serena, landing her a place at the Ostroff Center for recovery. Juliet proceeds to blackmail Lily for a monthly cheque by telling that she will reveal one of Serena's other dirty secrets if she does not provide her with cash. To avoid the wrath of Blair and others, Juliet leaves to return to her home town. A while later, Juliet sees Damien, Dan, and Blair getting into a car together, making her assume that they know all about what she's done and bringing her back to Manhattan to tell Serena everything. Serena and Juliet make peace when Juliet finds out that it was really Lily who signed the document that caused her brother sentenced five years in prison. Before she departs for her home town once more, Juliet promises not to cause harm to Serena or anyone else again.

Ben Donovan

Portrayed by David Call in season four, Ben Donovan is Juliet's brother who is in jail. He was Serena's English teacher for a brief time, and having spent some time together they both developed mutual feelings. When Serena returned to Manhattan, Ben was charged with statutory rape and transporting a minor across state lines. A crime of which was signed off by with Serena's very own signature. This caused him to be forced into serving a five-year sentence for a crime that he did not commit. He and Juliet devised a plot to destroy Serena's life permanently, however with no real intent on hurting her physically. In the end it was revealed that Lily, Serena's mother, had him put in jail by faking her daughter's signature so that Serena could return to Constance. Serena visits Ben to explain everything and to somewhat reconciliate.