Season 1, Episode 1: Pilot: Gossip Girl - Xoxo
Season 1, Episode 1: Pilot: Gossip Girl - Xoxo
At a privileged prep school for teens on Manhattan's Upper East Side, the students first learn that
Serena van der Woodsen is back in town the way they learn all the important news in their lives:
from the Internet blog of the all-knowing, albeit, ultra-secretive 'Gossip Girl'. No one knows
Gossip Girl's identity, but everyone in this exclusive and complicated vicious circle relies on her
website and text messages for the latest scoop. Even Serena's closest friend, Blair Waldorf, is
surprised to find that Serena has suddenly ended her self-imposed exile from a boarding school
in New England and returned to Manhattan for school. Once the Upper East Side's most
notorious party girl, Serena's reasons for returning are mysterious, although they may have
something to do with her younger brother Eric, who's secretly in the hospital following a suicide
attempt which is kept under wraps by their overprotective mother Lily. Whatever the reasons, the
change in Serena is obvious, especially to Blair, whose friendship with Serena has always been
competitive and difficult. Into this crowd comes Dan Humphrey, a kid from Brooklyn and whose
freshman sister, Jenny, tries a little too hard to fit into Blair's circle of gossip friends, whom
include 'Gossip Girl's contacts, Isabel and Kati. Blair's nice-guy boyfriend, Nate Archibald, is
also troubled by Serena's return for his best friend, Chuck Bass, the school's snobbish cynic and
resident bad boy, knows about a fling that Serena and Nate had which is why Serena left town to
avoid a scandal which, in the snobbish world of high society, is social suicide. Elsewhere, Dan
and Jenny's father, Rufus, a former rock musician and art gallery operator, also has a return of
feelings for Serena and Eric's mother, Lily.
Serena confides in Blair that she had sex with her boyfriend, Nate, right before she skipped town.
But Blair, being the person she is, vows a cruel revenge against Serina who decides that Dan
would make a good escort for the fund raiser brunch at the Palace Hotel... a brunch hosted by
none other than Jenny's would-be rapist, Chuck, and his uptight father Bart. Meanwhile, 'Gossip
Girl' posts on her web bloc that Jenny, the eager freshman, paid a visit to ultra-cool Blair, who
quickly realizes that granting the eager wannabe access to her elite inner circle might just prove
useful. Elsewhere, Lily meets with Rufus about how their lives went since they parted 15 years
earlier, and Dan discovers Lily's relationship with Bart, while Blair sends him running after she
tells him all about Serina's sordid past.
'Gossip Girl' narrates Ivy League week as the teens on the Upper East Side schools of Constance
Billard for Girls, and the rival St. Jude's for Boys, prepare for a much-anticipated visit from the
Ivy League representatives. The twisted and vindictive Blair, with Chuck's help, uncovers a
scandalous secret about Serena that may not remain a secret much longer which involves Eric
whom is still hold-ed up in the sanatorium. Dan has his heart and future set on the coveted usher
position for the Dartmouth rep, only to be beat out by Nate who has no interest in the school
despite pressure from his controlling father, The Captain. Meanwhile, Jenny bonds with Serena's
younger brother, Eric, who confides in her about his depression and recent suicide attempt, while
Rufus must swallow his pride and ask Lily for a favor to help Dan with a Dartmouth referral.
\
Blair is thrilled when her mother, Eleanor, chooses her to be the new face of her clothing line.
However, Blair's happiness soon turns to her typical feelings of betrayal and jealousy when
Serena moves into the spotlight and Blair finds herself back in Serena's shadow. Meanwhile,
Serena and Dan are reminded once again that they come from two very different worlds, and
Nate and Chuck indulge in a boys' weekend with the former trust-fund case, Carter Baizen, to
blow off steam after Ivy Week, and who gets the guys into trouble with some of his poker player
thugs. Elsewhere, Rufus bonds with an attractive art collector, named Bex, whom is interested in
his latest painting at the Bedford Avenue Art Gallery where he works.
\
Dan makes elaborate plans to impress Serena on their first official date. That same night, Jenny
is invited to the infamous Blair Waldorf sleepover and finds herself in a high stakes game of
"truth or dare." Meanwhile, when Lily discovers that Eric is missing from his treatment center,
she finds herself seeking help from her ex-boyfriend, Rufus.
\
Dan is torn between two girls when his childhood friend, Vanessa, returns home and declares her
feelings for him, just as he and Serena are trying to figure out what they mean to each other. At
the infamous masked ball, Blair sends Nate on a scavenger hunt, but Nate is ultimately still
distracted by his feelings for Serena. Although Blair makes it perfectly clear that outsiders are
not welcome, a disguised Jenny and Dan sneak into the ball. Elsewhere, Lily asks Rufus to
accompany her to an Eleanor Waldorf event in order to make Bart Bass jealous.
\
Things heat up between Serena and Dan when they admit they are in love with each other,
despite that they come from polar opposite worlds (she from wealthy Upper East Side
Manhattan, and he from working class Brooklyn). But Serena and Dan's plans to be alone to
consummate their romance is interrupted by Vanessa who shows up wanting to spend time with
Dan. Meanwhile, Chuck thinks of investing in a strip nightclub to make his father, Bart Bass,
proud of him. Jenny discovers a secret that her parents have been keeping from her. Also, Blair
is devastated by Nate's actions when Jenny reveals to Blair that Nate kissed her by accident at the
masked ball the night before after he mistook her for Serena. Blair, (being the cynical b*tch she
is), tells Jenny they are no longer friends. Nate's parents think that he should tell Blair he wants
to marry her, even though he doesn't have strong feelings for her. The Archibalds and Waldorf's
have a dinner party celebrating their new business deal together and it's obvious that Blair is
giving Nate the silent treatment. Nate confronts his father about the drugs he found in his house,
but he denies having a problem. The two get into a brawl and Nate's father punches him and as a
result Nate turns his own father into the police. Afterwards, Nate gets ready to go see Chuck at
the strip club he opened, but Blair stops him and tells him he needs to be with his father. Blair
tells Nate that she doesn't need him and they break up and she heads over to the strip club saying
she wants to "escape", which leads to a sordid tryst between Blair and Chuck in the backseat of
his limousine.
\
Blair is devastated by the current state of her relationship with Nate and the guilt from her recent
indiscretion. But she manages to put on a happy face for her 17th birthday party and attempts to
hide her feelings from her friends. Hoping to ease the tension between Serena and Vanessa, Dan
takes Vanessa to Blair's party so the girls can bond together, but this ends up making Serena
more uncomfortable. Jenny brings her mother, Alison Humphrey, home as a surprise visit. But
Rufus isn't ready to forgive and forget Alison for walking out on their marriage to find herself
and concentrate on her artist work. Also, Nate's parents ask him to make a huge sacrifice to save
his father's business as he faces charges of embezzlement and fraud.
\
Although it is Thanksgiving, hardly anyone has the holiday spirit. Blair and Serena have a fight
once Serena admits that she saw Blair with Chuck, and Blair orders Serena to keep it to herself.
Meanwhile, Nate and his family share a strained Thanksgiving meal before Mr. Archibald ends
up in the hospital after a suicide attempt. Having been uninvited by Blair to the Waldorf
Thanksgiving meal, the Van der Woodson family has dinner with the Humphreys at their loft in
Brooklyn, and the tension between Lily, Allison, and Rufus is palpable. Back in Manhattan in
the Waldorf penthouse, Blair revisits her bout of bulimia after discovering that her mother
forbade her father to join them for Thanksgiving. Throughout the entire episode, there are
flashbacks of last year's Thanksgiving involving how Dan met an stoned Serena for the first
time as well as Blair's Thanksgiving with her father and mother before their seperation. There is
a stark contrast between its joy and the present's strife.
\
As 'Gossip Girl' posts news of the annual Cotillion Ball to take place on the approaching
weekend, Blair decides not to go with Nate, but she finds herself being featured in The New
York Times and is enjoying her secret affair with Chuck. Serena decides not to go either, so her
grandmother, CeCe, shows up to change her mind. Meanwhile, Jenny volunteers for the ball and
Lily takes her under her wing. But the night of The Cotillion is the night of Alison's first art
opening, and Rufus and Alison tell Jenny that she cannot attend the ball. Jenny decides to defy
them both by secretly attending the dance anyway. Refreshed by Blair's newly buoyant attitude,
Nate asks her to the Cotillion and she accepts, which makes Chuck jealous. CeCe tells Lily and
Serena that she is sick with lung cancer and her last dying wish is to see Serena go to the ball,
and she wants Serena to go with the wealthy Carter Baizen. The snobbish CeCe takes an instant
dislike to Dan and she approaches Rufus with an offer pay him to convince Dan not to go with
Serena. Dan learns of this and tells Serena that he does not think very highly of CeCe by telling
Serena about how CeCe tried to bribe his father to persuade him not to attend. Surprisingly, the
skeptic Serena refuses to believe Dan that her compassionate grandmother is a crafty snob, and
she ends up going to the ball with Carter... both her and Dan having fallen right into CeCe's ploy.
Also, Chuck manipulates Nate into thinking Carter is having an affair with Blair to provoke a
fight with him.
\
Blair's estranged father, Harold, comes home for the Christmas holidays with an unexpected
guest: his gay lover Roman. Both Blair and her mother, Eleanor, find it difficult to hide their
disappointment while Blair hatches another underhanded plan to get rid of Roman for good.
Meanwhile, Jenny and Vanessa help Serena plan the best Christmas surprise ever for Dan, who
may have a surprise of his own in mind for Serena. Chuck phones Blair from Europe and
informs her that Nate has joined him in Monaco, worrying Blair that Chuck may disclose the
details of their hook-up. Also, Rufus refuses to remain the understanding husband any longer
after Alison's former lover calls the house.
\
Serena, Blair, Nate, Chuck and their entourage break into the school swimming pool for a night
of fun, but when a member of their group nearly drowns, the school threatens to expel the person
responsible for the break-in. Everyone agrees to keep a secret pact and say nothing, but it
ultimately creates major tension between Serena and Dan, who isn't sure he's ready to take the
fall for someone else and risk his future. Meanwhile, Vanessa is working on a documentary
project about private schools and accidentally captures Blair and Chuck discussing their affair.
Also, Lily contemplates telling Rufus how she really feels about him.
\
The shadowy and unseen 'Gossip Girl' takes pleasure in reporting that Serena was spotted by one
of GG's Web contacts buying pregnancy tests at a local pharmacy. Of course, on the Upper East
Side, the truth is often even juicier and more scandalous than the gossip when Dan's sister,
Jenny, learns that Serena was purchasing the tests for Blair who fears she might be pregnant
from her trysts with Nate. But things get worse when Nate finds out that Chuck has been having
an affair with Blair and both nearly come to physical blows, and Blair becomes ostracized by the
rest of her clique as her reputation of a slut becomes more known. Meanwhile, Rufus, in an
attempt to cheer himself up following his breakup with Lily, goes on a date with his art gallery
sponsor, Bex, to a local bar.
\
Spring Break is over, and so are all of Blair's days of hiding away. Finally, after three weeks, she
comes back to school, with an unpleasant welcome by Jenny and the "in" crowd, who throw ice
cream in her hair. Serena believes that being mean was got Blair kicked out of the "in" crowd in
the first place and dethroned "Queen Bee." When Jenny asks Blair to meet her at Butter along
with all of Blair's former friends, Serena finds it the perfect opportunity for Blair to show just
how nice she is. But the situation goes from nice to sour when Jenny and her friends purposely
don't show up, leaving Blair all alone. Meanwhile, Jenny needs something to wear for her 15th
birthday party, and eventually ends up stealing one of her friend's mother's dresses in exchange
for a $1,200 dress in an exchange shop. But when Jenny tries to get it back, she learns the red
dress is over $8,000. Once again, Jenny steals the red dress, throwing her coat over the dress.
She comes home to a 15th birthday party created by none other than Blair, who talked to Jenny's
dad, and made the birthday party as lame as possible. While Jenny's dad doesn't realize how lame
the party is, Jenny's friends do, and are about to leave when they find Jenny wearing the red
dress. They ditch the birthday party and meet Blair at Butter. Thinking quickly, Jenny sneaks out
and has Nate accompany her to Butter. Jenny's friends are pleased that Nate, who they are
attracted to, is hanging out with them, and "forget" the incident with the dress, leaving Blair
friendless once again. Also, Serena adjusts to her new living conditions with Chuck, but when
she receives inappropriate gifts, she believes Chuck sent them. But, at the very end of the
episode, she learns who really sent them, and it wasn't Chuck.
\
Serena's world becomes chaos when a former friend-turned-enemy, the evil and sociopath
Georgina Sparks, returns to town and transfers to her school. Dan sees Serena preoccupied and
he assumes that it has something to do with the nasty Chuck, who's looking forward to making
her life a living-hell as her soon-to-be step-brother. Nate connects with the last person he
expected, Vanessa over his failed relationship with Blair. Serena goes out with Georgina for a
night on the town to try to patch things up between them, but things get so bad that Serena thinks
someone spiked her drink. Meanwhile, Hazel and Penelope try to recruit newcomer Nelly Yuki
to be part of their gossip club, but it is not easy. Blair supervises the whole operation and hatches
a plan to sabotage Nelly. When Nelly breaks down after being reminded of her recent break-up
with her boyfriend, the ladies find their way in and Nelly comes to the Waldorf penthouse where
Blair tries to repair the damage. Elsewhere, Jenny develops a crush on 16-year-old dog-walker,
Asher Hornsby, who might be her ticket to permanent popularity.
\
Georgina tells Serena that she can reveal a deep dark secret from Serena's past, but no one is
prepared for what Georgina does next. Meanwhile, Blair and Jenny's power struggle continues
when each of them start spreading false and scandalous rumors about each other on Gossip Girl's
blog. Dan sees Jenny's new beau Asher cheating on her and tells her, but Jenny refuses to believe
Dan. Rufus goes to Lily for advice on how to handle Jenny's new rebellious behavior. Serena
tries to confront Georgina, but she skips town before Serena has a chance. After this, Serena tells
Lily and everyone she and Georgina are not friends after discovering that Georgina has been
lying to everyone, claiming that she and Serena are still friends.
\
Serena falls back into her old habits of drinking and drugs. She eventually reveals to Blair true
reason why she left Manhattan: to avoid being implicated in an accidental drug overdose of a
school friend in which Georgina was also present. Blair, Nate, and Chuck are forced to team up
to try to help Serena deal with this situation. Unfortunately, Serena is too ashamed at herself to
share the truth with Dan about her mistake, and therefore he naturally assumes the worse about
his girlfriend. Lily discovers the blackmail videotape Georgina made showing her and Serena
that night with their victim. Being who Lily is, she too jumps to the wrong conclusion about
Serena and it takes a little intervention from Blair to save her friend from being emotionally torn
apart for good. Blair also discovers from Vanessa that Georgina, under her alias 'Sara', is still
hounding them by pretending to be their friends, and Georgina takes advantage of Dan's
alienation with Serena to make the moves on him. Meanwhile, Rufus is excited when his band is
invited to perform at a Rolling Stones sponsored concert. But Lily is the last person on Earth he
expects to see at the performance, especially since her wedding rehearsal dinner is on the same
night.
\
Blair takes matters into her own hands to help Serena deal with the manipulative and evil
Georgina Sparks who threatens to expose Serena's secret. Lily, while keeping Rufus in her mind,
prepares for her wedding with Bart Bass that is designed to be the Upper East Side's social event
of the year. Serena finally tells Dan the whole truth about her past and about Georgnia and they
try to work things out. But Dan is guilt-ridden after having cheated on Serena with Georgina and
wonders if it is already too late. An unexpected guest shows up at Lily and Bart's wedding. Also
Blair manipulates matters so that Georgina goes "somewhere where she can do no harm". As the
end of the school year approaches, Blair plans to go somewhere with Chuck.
As the summer of the Upper East Siders comes to a close, Blair returns from her summer trip to
Europe with a charming new boyfriend, named James, just to make Chuck jealous when she
takes him to the Hamptons to spend the last few weeks of the summer with her. However, 'James'
is hiding a secret of his own from everyone. Serena, struggling to get over her breakup with Dan,
takes a liking to a young lifeguard. Meanwhile, Nate gets involved in a steamy relationship with
an older woman, named Catherine whom is married. While Rufus is still on tour with his band,
Dan has remained in New York to take a job with a demanding magazine editor, and has gone on
a dating spree to get over his breakup with Serena, while Jenny has taken a job at a fashion
company working under the cynical, devil-incarnated Laurel, who holds Jenny back for she sees
ambitious interns as a threat to her own job.
As Blair struggles to adjust herself to her British boyfriend, Lord Marcus Beaton's ways, he
introduces her to his parents, where the identity of Lord Marcus' mother is revealed. At the
Beaton party, Chuck tries to make Blair jealous when he shows up with Catherine, Nate's secret
love interest. Meanwhile, Nate and Serena get closer while he tries to keep far away from
Catherine, while Serena begins to have doubts about re-staring her romance with Dan. Chuck
and Marcus Beaton begin an unexpected friendship, and Blair makes a revelation.
Serena and Dan are trapped in an elevator during a citywide blackout which makes them trying
to work out their differences. Meanwhile, Marcus and Blair have problems of their own which is
passion. Chuck realizes that he has problems in having no passion with women other than Blair.
Elsewhere, Nate struggles with his feelings for Vanessa and Catherine.
When Dan starts getting cozy with Amanda, the new girl at school, Serena turns to Blair and her
minions to step in to sabotage her chances. Vanessa also enlists Blair's help when she finds out a
scandalous secret about Catherine.
As Gossip Girl narrates the so-called Fashion Week where the students of the Upper East Side
gather for the annual fund raiser, Blair becomes angry with her mother when she gives Serena
and her new socialite friend, Poppy Lifton, front row seats to the Eleanor Waldorf Fashion
Show. Hurt and betrayed by both Serena and her mother, Blair decides to sabotage the show.
Meanwhile, Dan, also humiliated and shunned by Serena (who has fully returned to her former
bad-girl self), starts hanging out with Chuck and his life of parties. Dan quickly learns that living
the life of the dark side has its risks. Also, Lily learns a secret that her new husband, Bart Bass,
has been keeping from her.
Serena decides to visit Yale and gets even with Blair. Dan learns that none of his
recommendation letters made it to Yale.
Season 2, Episode 7: Chuck in Real Life
Vanessa begins her own slide on a dark path when she tries to blackmail Blair into being a nicer
person, with the photos she took of Catherine and Marcus. Blair then seeks revenge by
convincing Chuck to try to seduce Vanessa to steal her phone camera. Meanwhile, Lily and Bart
throw an extravagant housewarming party and expect their children to make them proud, but the
Serena do not want to follow the rules when she correctly suspects Bart to be influencing Lily to
do what he wants for business and self-interest. Elsewhere, Dan and Jenny discover a big secret
that Nate has been keeping from them.
Jenny has a new young model friend, named Agnes, who encourages Jenny to explore her wild
side, and also to confront Eleanor Waldorf who is planning to steal Jenny's designs in order to
pass them off as her own. Meanwhile, Serena and Dan attend Rufus' latest art opening as friends,
but then Serena meets an artist, named Aaron Rose, and the evening gets a little uncomfortable
for Dan. Elsewhere, Blair attempts to seduce Chuck, but he proves to be tougher than she ever
imagined. Also, Jenny begins to have a mutual feelings with Nate as he's staying with her, Dan,
and Rufus while searching for a place to live.
Serena invites Aaron to be her guest at a charity gala honoring Lily and Bart, but after
discovering a secret that Aaron has been keeping from her, Serena begins to question whether
Aaron 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. But the teenager,
Emma, proves to be more than a handful and Blair begins to suspect that the evening may
actually wind up hurting her chances of getting into the college of her dreams. So, Blair forces
Serena and Chuck to help her find the trouble making teen when she takes off. Meanwhile,
Vanessa discovers the relationship between Nate and Jenny, in which Jenny is planning with
Agnes a guerrilla fashion show by crashing Lily and Bart's gala with th hope that it will either
launch Jenny's career or ruin her chances of ever being accepted by the industry. Dan angrily
tells Nate to move out of the apartment, while Rufus tries to deal with the rebellious Jenny.
Blair is against the idea of her mother, Eleanor, with a new man in her life, named Cyrus Rose,
and she in her natural and evil ways, does everything in her power to make it impossible for
them to be together by trying to break them up when Cyrus throws Blair a party for her 18th
birthday. Meanwhile, Jenny and Agnes move in together against Rufus protest, while they try to
look for a buyer in the wake of Jenny's fashion show. But when Jenny goes behind Agnes back
to exclude her from their business when Agnes cannot be counted on for her slacking off, Agnes
learns about Jenny's betrayal and retaliates by setting fire to all of Jenny's designs and throws her
out onto the street. Elsewhere, Serena and Aaron fall for each other, but something about Aaron
threatens to ruin their new relationship as well as Aaron's father whom happens to be Cyrus.
Also, Dan and Chuck are at war again due to Dan's true interest in Chuck's father Bart over his
past business deals.
As Thanksgiving draws near, Blair looks forward to spending the holiday with her family. But
her disappointment only begins when her father, Harold, is delayed in trying to leave Europe,
and Eleanor's new boyfriend, Cyrus, takes over planning the traditional Thanksgiving feast. Blair
also learns that Cyrus plans to propose marriage to Eleanor, which prompts her to run into the
company of her Polish maid, Dorota. Serena continues to hide her sordid past from Aaron after
he tells her that he too is a recovering alcoholic and party guy. Meanwhile, Dan asks Lily to help
intervene in the continuing feud between Jenny and Rufus when Jenny crashes at Lily's
penthouse and confides in her that she has decided to file a petition to become legally
emancipated from her father. Eric also learns from Chuck about Bart's investigation and files he
keeps on everyone to keep everyone and everything under his iron thumb. Elsewhere, Nate's
fugitive father, Howie 'The Captain' Archibald, arrives in town to visit him and his mother with
an offer to live a life of luxury as fugitives, while Vanessa gets caught up when the authorities
comes to call her on Mr. Archibald's whereabouts after he's spotted re-entering the country.
The teens prepare for the annual Snowflake Ball, a charity event for prep school seniors.
The entire Upper East Side of Manhattan is rocked when Bart Bass dies suddenly in a limo
accident. Serina and Eric takes the news very calmly while Lily has a troubling time despite her
mother, Cece's, awkward attempts to comfort her. Chuck begins to blame Lily for his father's
death and threatens to reveal a secret that Bart found on her before his accident. Meanwhile,
Blair's mother, Eleanor, prepares her latest marriage to Aaron's father Cyrus.
Because Chuck has been missing since his father's funeral, his Uncle Jack, Bart's younger
brother, arrives in New York to help Lily find and help him. Trying to forget her last unpleasant
conversation with Chuck, Blair focuses on being accepted into the most prestigious ladies club in
the city, the Colony Club. Meanwhile, Jenny returns to school at Constance Billard and
immediately takes on Penelope, Hazel, Nelly, Isabel, and the rest of the mean girls. But Jenny is
not willing to go down without a valiant Gossip Girl-worthy fight against these bullies.
Season 2, Episode 15: Gone with the Will
At the reading of Bart Bass' will, Chuck is bequeathed the majority share of Bass Industries, but
Jack soon manipulates Chuck into giving him the company. Chuck decides to take over the
company after being persuaded by Blair. Blair throws a surprise party for Chuck and invites the
board of the Bass company. Jack sabotages the party leading the board to elect Jack as the
president. Meanwhile, Rufus and Lily travel to Boston to look for their out-of-wedlock son by
trying to make contact with the adoptive parents, but they are eventually deceived into thinking
their child is dead. Back in New York, Serena's relationship with Dan is almost ruined when she
finds out about the half-sibling she shares with him.
Serena, Blair, Dan, and the rest of the seniors try to find out who is worthy of an early admission
to Yale. Serena discovers that she has been accepted, but concedes the acceptance to let Blair
take the position because of what Blair will do as a result. Serena also connects with a young
new Shakespeare teacher, Rachel Carr, who has no clue about what is going to happen when she
gives Blair the first 'B' grade in her life, but Blair soon comes to learn that she may have met her
match against this latest addition to her school. Meanwhile, Chuck reluctantly joins forces with
Lily in his war against his manipulative Uncle Jack over controlling Bass Industries. Also, Nate
and Vanessa plan to take their romance public by attending a romantic night date at the opera,
while Lily wants to do the same with Rufus despite his loathing of the wealthy high-society
world, and of her reputation in the community over recent events.
The twisted Blair plans a cruel revenge against her teacher, Rachel Carr, for her one bad grade,
but has problems getting her posse of mean girls to rally for support since they are not keen to
taking on a teacher. So, Blair starts a rumor that Miss Carr and Dan are romantically involved,
which creates a firestorm of gossip, and she has her father, Harold, to back her up. But the final
blows comes when Serena sees Dan and Rachel meeting at a local coffee shop and jumps to the
wrong conclusion which Blair sees off her greatest victory, but also her most bittersweet one.
Meanwhile, Chuck calls upon Nate and Vanessa for help when he wakes up in a strange hotel
room and seek out a mysterious woman he met at a mysterious secret society party the night
before which may had drastic consequences for him.
As Constance Billiard prepares for the annual school play of 'Age of Innocence' the frantic
production threatens to break the whole school apart as, Dan continues to ignore Serena and
continue his dirty tryst with Rachel Carr. When Blair learns that her acceptance into Yale went to
Nelly, she suspects Serena of leaking info about her detention stint, while Serena blames Blair of
babbling about her own problems. But the real culprit it Rachel who is seeking to get back at
Blair for destroying her career. Rufus and Jenny learn about Dan's relationship with Rachel Carr
and try to force him to end it. Nate becomes jealous when he thinks that Vanessa is flirting with
the play director Julian, while it is Serena who has the crush and asks Vanessa for pointers
Meanwhile, Chuck becomes more intrigued and frustrated as he tries to dig deeper into the
mystery about his late father and what connections he had with the super-secret underground
society which leads him to try to find the shadowy Elle, who warned him about investigating the
secret society.
Devastated by the recent plot twist in her life, Blair turns her back on her predictable Waldorf
existence in favor of a wild, unpredictable lifestyle that includes Carter, 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 Kennedyesque family, The Vanderbilts, who
abandoned Nate and his mother when they needed them most. Elsewhere, in a misguided effort
to be completely honest with each other, Lily and Rufus agree to share lists of their past lovers.
Serena decides to throw Jenny an intimate party for her 16th birthday, but things get out of
control when Serena's friend Poppy Lifton, returns and turns the small gathering at the van der
Woodsen apartment into a huge social event. Meanwhile, Vanessa agrees to help Chuck with a
scheme that will make Blair and Nate jealous... and they end up having sex in the process. Also,
Rufus learns that Dan and he will not receive financial aid at Yale and tries to figure out another
way to cover the cost of his education, in which Lily offers to help. Elsewhere, Dan receives a
letter from Boston from Rufus and Lily's illegitimate son wanting to meet with him.
Serena returns from her week-long trip to Spain with Poppy and Gabriel. But Serena becomes
worried that during the hard partying in the country, she thinks she may have gotten married to
Gabriel by accident. Meanwhile, Blair makes a secret deal with Nate's grandfather, William, to
influence Nate to attend Yale when he decides to defy his grandfather and attend Columbia
University in New York City instead. Later, Nate learns some disturbing information about his
father's arrest while he is asked to be the best man at his cousin Trip's upcoming wedding. Chuck
continues his debauched lifestyle of one-night stands while Jenny decides to make a stand for
herself against the loathsome guy. Elsewhere, Dan takes a job as a waiter to earn money for
college. H is distressed to find out that the job is a Passover Seder at the Waldorf penthouse that
Cyrus holds, and on top of that... several of his friends and family are guests, including his father
Rufus.
Blair pressures Georgina into making amends for her past bad behavior by helping her in a
scheme to rip off Poppy after she has embezzled all of the investment money that she and
Gabriel claim to invest in. Meanwhile, the rivalry between Nate and Chuck over Blair comes to a
head. When Lily learns that Poppy scam ed her of Rufus's investment money, she hatches a
secret plan to help Rufus with Dan's college tuition in order to cover up Poppy's scam out of
shame. But Serena has a plan to make Poppy pay for all the cheating he did, but Lily is not in
agreement and takes drastic measures which ruins everything.
Lily recalls her past when in a flashback to 1983, the naive and sheltered 17-year-old Lily
Rhodes got kicked out of her Santa Barbara boarding school. She ran away to Los Angeles
where she tried to re-connect with her divorced and dysfunctional parents; her workaholic record
producer father, Rick Rhodes, and the superficial Cece. Lily also met and hooked up with her
outgoing free-spirited 19-year-old sister Carol. Carol was the so-called "black sheep" of the
family who introduced Lily to the life of partying, as well as Owen, a busboy at Carol's place of
employment. Eventually, they all got arrested after crashing a party hosted by the cynical and
mean music producer Keith van der Woodsen (Lily's future husband) whom attempted to
swindle Carol out of a music deal. In present day New York, Blair and Nate decide to attend
their senior prom together. But the evening doesn't turn out exactly as planned, when the Mean
Girls attempt to rig the votes for prom king and queen. But Chuck comes to Serena's rescue.
Meanwhile, Serena becomes furious when she learns that Lily deliberately had her arrested for
her defiance, while Rufus ponders his life and future without Lily, who he snubs for what she did
to Serena, as does Eric, Jenny, and even Dan as well whom is forced to bail Serena out of jail
himself.
Gossip Girl decides to liven things up at the Constance Billard and St. Jude's graduation by
sending out a shocking and damaging email blast in the midst of the commencement ceremony,
stirring Serena to come up with a plan of attack. The Mean Girls; Nelly, Isabel, Penelope, etc,
challenge Jenny to throw her hat in the ring to succeed Blair as Queen Bee next year.
Meanwhile, Lily and Rufus finally makes amends meet and get engaged and move in together.
With Blair's blessing, Jenny becomes the new queen. Chuck finally admits his love to Blair and
the two reconcile. As the summer draws near, Nate decides to go on the backpacking trip with
Vanessa. Georgina returns to town having recovered/re-stole all of Dan's money, and she also
requests Blair for a roommate at NYU. Carter Baizen also shows up and reveals to Serena where
her biological father is. In the end, Serena is going to Brown, Blair, Dan, Vanessa, and Georgina
are going to NYU, and Nate is going uptown to Columbia, and Lily and Rufus' illegitimate son,
Scott, inconspicuously arrives in town for college and to shadow Dan.
As the summer is drawing to a close, Blair and Chuck are madly in love and adjusting to their
new "in a relationship" status, breaking all the traditional rules of dating as would be expected.
Serena returns from her European adventure with many secrets to hide and a complicated
relationship with Carter Baizen. Nate returns from his travels with a mysterious brunette, Bree
Buckley in tow. Rufus, Dan and Jenny spent the summer in the Hamptons, adjusting to the van
Der Woodsens' glamorous lifestyle surprisingly faster than any of them expected. Meanwhile,
Vanessa begins a relationship with Scott, not knowing that is the lost brother of Dan and Serena.
Blair, who is determined to maintain her Queen status in college, embarks on her first day at
NYU, along with Dan and Vanessa. Unfortunately, Georgina turns up as Blair's roommate in the
dorms, determined to make Blair a social outcast. As Serena prepares to depart for Brown, she
and Chuck have a major falling out, so she recruits Chuck's enemy, Carter, to help her get even.
Nate and Bree decide to explore their relationship further, knowing full well that it could cause
tension between their families who are political rivals.
It's an Upper East Side face-off when Blair and Chuck both set their sights on a particular item
up for bid at Sotheby's and the personal stakes are high. Serena suspects that Carter may be up to
his old habits, Georgina takes an interest in Dan, and Vanessa begins to suspect that something
isn't quite right with Scott.
On the first day of school at Constance Billard, Jenny is forced to make her rightful place as the
new Queen Bee of the Mean Girls. Unfortunately for Jenny, Blair is more than happy to
intervene when news reaches her that Jenny may need her help. Meanwhile, Lily finally returns
home to Rufus and her family to find that things are definitely not as she left them, especially
after learning that Serena has decided against going to Brown University. Elsewhere, a famous
teenage movie actress, Olivia Burke, enrolls at NYU and is assigned as Vanessa's new roommate
in which Olivia hopes for a somewhat normal college experience. Also, Olivia's best friend
Ursula, another actress co-starring in Olivia's latest movie, befriends Serena.
Lily and Rufus decide to move up their wedding to the next day, but a series of complications
threaten to tear them back apart again. Meanwhile, Chuck discovers a secret that Carter has been
keeping from Serena which involves Nate's girlfriend Bree and her family whom are out to get
Carter. Dan and Vanessa are pulled into one of Georgina's schemes when she threatens to ruin
Lily and Rufus' wedding by revealing the secret about Scott Rosson as their illegitimate son.
Also, Blair is suspicious of Bree and shares her concerns with Nate that she may have an agenda
regarding him and Carter.
Vanessa and Blair both take to scheming to be given the honor of giving the freshman toast at
NYU. Meanwhile, Serena and Nate try their hand at poker in hopes of winning Carter back from
the Buckleys, and Dan wants to introduce Olivia to Rufus and Lily.
Chuck decides to move up his hotel nightclub's opening and enlists Serena's help to get the word
out to her celebrity clients for publicity reasons. Feeling left out of the planning, Blair attempts
to win Chuck's approval by secretly helping him with a problem concerning opening night.
Meanwhile, Dan is unnerved when he finally watches one of Olivia's infamous simulated sex
scenes in one of her movies with co-star and real-life boyfriend at the time, Patrick Robinson.
Jenny is forced to choose between her friendship with Eric and her new role as Queen Bee of
Constance Billiard since she and the Mean Girls are not required to have any friends, except the
ones their own vicious and cynical circle. Elsewhere, Rufus gets Lily into the Halloween spirit
by taking her out to a costume party.
Olivia says something she regrets during her appearance on Jimmy Fallon's TV talk show and
tries to keep Dan from finding out. With the local election day around the corner, Nate suspects
that his grandfather will stop at nothing to get his cousin 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.
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. Meanwhile, 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.
As Thanksgiving draws near, Blair suspects her mother, Eleanor, has been keeping a big secret
from her, but it turns out to be something else entirely. Meanwhile, Vanessa is supposed to spend
Thanksgiving with her parents, but has a fight with her picky and estranged mother and she ends
up going to Dan's loft. Rufus discovers that Lily has been lying to him about the true nature of
her mother Cece's health. Chuck tells Nate that he has some potentially damaging information
about one of their friends: Serena whom is caught in a compromising position with Trip
Vanderbilt. Elsewhere, Jenny learns that Eric was behind her very public embarrassment at
Cotillion and can't pass up a chance to get even with him in the most cruel way, which makes her
appear even more vile and twisted than everyone else around her. Also, Serena is put in a very
awkward position when Lily invites Trip and his wife, Maureen, to join them for Thanksgiving
dinner at their penthouse, and Maureen may know a lot more about what is going on between
Trip and Serena than she claims to, and Doroda is revealed to be hiding a secret of her own
involving Vallini.
On the anniversary of Bart Bass' death, Chuck wrestles with the dilemma of following his
conscience, or that of his father. Serena begins to suspect in Trip, when thank Nate, discovers
that has been joined by Maureen. Dan and Vanessa attempt to navigate their newly complicated
friendship. Eric and Kira make work his plan to dethrone Jenny. Meanwhile, the relationship
between Lily and Rufus deteriorates when he discovers the letter from Serena's father.
Nate and Serena decide to explore the boundaries of their friendship. Blair suspects that Chuck is
having problems forgetting about the woman he saw at his father's grave. Jenny agrees to
accompany Damien to a State Dinner, but she realizes that his plan is ruined by a memory of the
school. Dan tries to overcome the confession of love for Vanessa, without any result. Rufus
returns from a ski trip and tries his best to avoid Lily.
Despite being grounded, Jenny continues to see Damien who tells Jenny that he wants to have
sex with her. Lily thinks to tell the secret that she has supported conceal, but after a call, she
changes of mind. Dan and Vanessa explore a new stage of their friendship. Chuck is forced to
make an extremely difficult decision about his hotel. Meanwhile, Serena and Nate have a fight
that is reminiscent of past events.
Chuck finds himself once again at odds with his uncle, Jack Bass. Eleanor puts Blair in charge of
making sure her latest fashion show is a huge success with an important client. Rufus attempts to
get Jenny back on track by volunteering to have her help with Eleanor's fashion show, but the
opportunity takes a big turn for the worse when Jenny learns that Agnes will be one of the
models.
Chuck and Blair are faced with the most difficult decision they have ever faced as a couple.
Serena plans a surprise birthday party for Nate, but Jenny does her best to sabotage Serenas's
efforts. Dan and Vanessa's new relationship hits a bump in the road.
Chuck offers to throw a wedding for a very pregnant Dorota who insists that she and Vanya have
a traditional wedding before her parents arrive from Poland and find their daughter pregnant and
without a husband. Dorota asks Blair and Chuck to be part of the ceremony and walk her down
the aisle. Serena tells Nate she is having breakfast with the Humphreys when in reality she's
secretly meeting up with Carter Baizen. Rufus discovers that Lily has been lying to him about
her whereabouts.
When Lily's ex-husband, Dr. William van der Woodsen, shows up unexpectedly in Manhattan,
Serena finally gets the reunion she has so desperately wanted with her father, but the
circumstances turn out to be far from ideal. When Serena and Nate continue to have relationship
issues, a scheming Jenny is more than happy to be a shoulder for Nate to lean on. Meanwhile,
Dan finds out that he didn't get accepted into the Tisch writing program and Vanessa admits she
may have been somewhat responsible.
Will's return to the Upper East Side continues to stir up problems for Serena, Lily and his long-
standing rival, Rufus. Serena and Jenny's relationship is strained as a result of Jenny's deception.
Blair spends time on the Columbia campus and realizes where she truly belongs. Dan learns that
Vanessa has been keeping yet another secret from him.
When things get tense between Rufus and Will, Serena chooses to stand behind her father, while
at the Rufus is made to feel like an outsider in his own family. Meanwhile, Jenny deliberately
shares information with Will that may ultimately destroy Lily and Rufus' marriage. After many
failed attempts, Chuck makes one last grand gesture to reconcile with Blair, hoping she will
finally accept the fact that they are destined to be together.
Blair must decide whether to meet Chuck at the top of the Empire State Building or risk losing
their future together. A Gossip Girl gossip bomb involving Dan explodes Serena and Nate's
relationship. Dorota and Vanya welcome their baby. Jenny hits rock bottom. Georgina returns to
the Upper East Side...and she has an agenda.