Serena is considered the "It Girl" of the Upper East Side. Throughout the series, Serena has an on-again, off-again relationship with Dan Humphrey and the two have the longest running relationship on the show; spanning from Pilot to their marriage in the season six finale, New York, I Love You XOXO. She is best friends with Blair Waldorf and shares close friendships with Nate Archibald and Chuck Bass.
Serena van der Woodsen is the daughter of William and Lily van der Woodsen. The story begins with her return to New York from boarding school. Shortly after her return, she realizes a lot has changed since she left; including her friendship with her best friend, Blair Waldorf.
She then meets Dan Humphrey and the two begin a romantic relationship and soon fall in love. Serena's storylines often surround her disastrous relationship choices and her struggle to find where she fits in the world outside the Upper East Side. In the finale, Dan and Serena get married, surrounded by friends and family.
Serena is described as a tall, blonde, slim, and beautiful teenage girl from the Upper East Side of Manhattan in New York City. She is not particularly academically skilled, but she is often told that she is not meeting her full potential.This continually causes problems with her best friend, Blair Waldorf, as Serena is able to waltz her way easily through life while Blair has to work for things Serena attains via her charm. Her father, William van der Woodsen, runs the same Dutch shipping firm his great-great-grandfather founded in the 18th century, and her mother, Lillian van der Woodsen, is a socialite, art collector, and philanthropist. Her mother and father are on the boards of all major charities and art organizations in the city. She also has an older brother, Erik, who attends Brown University. The van der Woodsens reside at 994 Fifth Avenue, a ritzy, white-gloved doorman building directly across the street from The Met and Central Park. Serena and her family own half the top floor in a 14-room penthouse.
Serena has a nail-biting habit and also cuts her split ends off, mainly during her classes at school. Though exposed and aware of the on-goings in the fashion world, she, unlike Blair, is not as meticulous about her fashion choices and wardrobe. Serena goes to Yale at the end of the series. Similar to the television adaptation, she dates a variety of different boys, including Nate, whom she lost her virginity to. Through the books, she realize that she truly loves Nate, but he is still Blair's boyfriend. In the thirteenth novel, she decides to stay in New York to be with Nate, but at the end, he leaves to not get in between her and Blair.
The series begins with Serena's return to the Upper East Side after spending a year in Cornwall, Connecticut, attending The Knightley School. Upon arriving home, she rejects romantic advances from both Chuck Bass and her best friend Blair Waldorf's boyfriend, Nate Archibald. She also reconnects with her mother, Lily van der Woodsen, and her recovering brother Eric van der Woodsen, who is in rehab after attempting suicide. After a chance meeting at the hotel where she is staying with Lily, Serena meets Dan Humphrey and the two begin a romantic relationship (Pilot). Soon after, Nate reveals to Blair that he slept with Serena before she left town and as a result, Blair begins to ice Serena out of her world (The Wild Brunch). During Ivy Week, Blair publicly outs Serena for having alcohol and drug problems in front of representatives from several Ivy League schools. Afterwards, Eric tells Blair he is the one in treatment; which leads to a reconciliation between Blair and Serena (Poison Ivy).
In Roman Holiday, Serena and Eric learn that Chuck's father, Bart Bass, is going to marry Lily. After spring break, they move in with the Bass' as they prepare to blend their households. The move ultimately shakes Serena more than she anticipated and it begins to cause problems in her relationship with Dan (The Blair Bitch Project). Things take a turn for the worse when Serena's old frenemy, Georgina Sparks, returns to town. They begin to hang out again but Serena asks her to stay away when she misses the SATs after a night out with her. Angry, Georgina befriends Dan using an alias as a girl named Sarah (Desperately Seeking Serena).
Scared of what will happen next, Serena goes to Blair and tells her the major secret Georgina has on her: that she killed someone. After her revelation, she leaves and Blair eventually finds her, drunk and messed up. She asks Nate and Chuck to help and after she's cleaned up, Dan comes by to see her. He asks her what is going on and she lies that she cheated on him. Hurt, he leaves the apartment leaving Serena with Blair, Nate, and Chuck. She then tells them the whole story: that after she slept with Nate at the Shepherd wedding, she went to meet up with Georgina and a mutual friend, Pete Fairman. However, unbeknownst to her, Georgina had set up a camera to film her having sex with Pete. When Serena arrived at the hotel, she began to make out with Pete but didn't do anything, suggesting he take a line of cocaine before they do anything else. He does so, but overdoses and begins seizing. She and Georgina leave the hotel room but not before she calls an ambulance. Afterwards, she waited across the street, wanting to see Pete being revived: but instead saw him being wheeled out in a body bag. Feeling guilty for his death, she left for Connecticut.
Later that day, Serena attends Lily and Bart's rehearsal dinner, but after Lily learns the real story, she takes Serena to meet with Pete's parents and absolve her guilt. Once she does so, she goes looking for Dan but finds that Georgina is with him and planning to sleep with him as revenge for Serena outing their secret (Woman on the Verge)
The next day, Serena tells Dan the whole truth. He then teams up with Blair to take Georgina down and they succeed. At the wedding, he breaks up with Serena; blaming her lies and the fact that they just come from too different worlds. She then leaves to spend the summer in the Hamptons (Much 'I Do' About Nothing).
The first episode of the second season (Summer Kind of Wonderful) begins in the Hamptons, where Serena is rumored to be dating Nate. However, it is a lie concocted by them both so Nate is able to have an affair with an older, married woman and Serena can grieve her relationship with Dan ending. After a few mishaps during The White Party, the two resume their relationship.
The couple's return to New York (Never Been Marcused) has them returning to old issues as Dan struggles with the differences in their lifestyles and eventually is unable to deal with those differences. The two end their relationship in an elevator during Blair's party, having succumbed to their relationship problems during a blackout (The Dark Night).
Gossip Girl cites the new school year and Serena's newly single status as a possible return of Serena as the Queen Bee of Constance as senior year begins. Serena, however, attempts to adjust to a purely platonic relationship with Dan, but she is hurt to find out that he has easily moved on from their relationship when he starts dating new student Amanda Lasher. Blair intervenes by torturing Amanda so she will distance herself from Dan, leading Serena to apologize to both Dan and Amanda and inviting them out for drinks; during which Dan wrongfully assumes Serena is trying to sabotage their relationship. A hurt Serena asks Dan to leave, but at the same time Isabel and Penelope ruin the night by throwing a Nairtini at Amanda. A frustrated Amanda leaves and Dan lashes out at Serena, who is innocent of the incident, and tells her that she should own up to her real self. Serena, angered at Dan's accusation, confronts Blair's clique and tells them that the next time that they mess with Dan, it has to go through her first. Her statement indicates her return as the Queen Bee. The next morning brings back Serena and Blair's old rivalry, as the girls fawn over Serena and ignore Blair in favor of her. Serena publicly ostracizes Dan at the courtyard connecting Constance and St. Jude's, followed by Blair's clique (The Ex-Files).
Serena and Blair's rivalry escalates in The Serena Also Rises during Fashion Week as the girls at school continue to fawn over Serena after seeing her with Poppy Lifton, her new socialite friend that brings her public praise and media attention. After Blair tries to win her friends back by inviting them to Eleanor's fashion show, Serena attempts to reconcile with Blair but is turned her down. Later, Blair becomes upset when she finds out that her mother has given Serena and Poppy front row seats at her show and Serena will not be backstage with her as usual. She tries to sabotage the fashion show but it ends up being a huge success and bumping Serena's popularity; which makes Blair even more jealous.
In New Haven Can Wait, Serena, angry at Blair after she tore into Serena after the fashion show, decides to attend an interview at Yale University, where Blair always dreamed of attending. Serena impresses Dean Berube and is given an invitation to a private reception at his home. Shocked at seeing Serena at the school, Blair accidentally ruins her interview but is able to bribe her way into the party. After a game gone wrong, Blair and Serena end their friendship and part ways. The next day, they make up after realizing they need each other.
Serena begins a romance with Aaron Rose, an artist and Blair's future step-brother in Pret-a-Poor-J. She accepts his offer to travel to Argentina with him but they break up soon into the flight after Serena realizes she still has feelings for Dan (O Brother, Where Bart Thou?).
After she returns from Argentina, Serena and Dan get back together (In the Realm of the Basses). But soon after, they discover that their parents, Lily and Rufus, had a child together who was given up for adoption before either of them was born (Gone with the Will) which causes tension between the two. Meanwhile, Dan befriends Serena's Shakespeare teacher, Rachel Carr, and Serena begins to suspect the two are having an affair. After seeing them hug at a dinner alone, Serena tells Blair, who informs Headmistress Queller and the parent committee. Once this is out in the open, Serena and Dan break up, realizing they can't overcome the recent issues between them (Carrnal Knowledge).
Toward the end of the season, Serena begins a relationship with Gabriel Edwards (Seder Anything), a man who seemingly left his girlfriend, Serena's friend Poppy, for her. After getting Lily and their Upper East Side friends to invest in Gabriel's business that supposedly brings the internet to third world countries (Southern Gentlemen Prefer Blondes), Serena realizes that both he and Poppy are conning them. She, along with Blair, Nate, and Chuck and the newly born-again Christian Georgina hatch a plan to catch them. However, the plan does not work out when Lily has her arrested for not stopping when asked. Gabriel and Poppy escape (The Wrath of Con).
In the final episode of the season, The Goodbye Gossip Girl, Gossip Girl sends a blast during their graduation commencement ceremony, denouncing Serena as irrelevant. Serena, angry and hurt that Gossip Girl has ruined the day, vows to find out who she really is. However, her plan fizzles out and they never find out. At the end of the episode, Carter Baizen, an old friend, tells Serena he has found the whereabouts of her father, William van der Woodsen. Serena decides to go with Carter to meet him before she leaves to attend Brown University in the fall.
At the beginning of the season during the summer, Serena had been searching for her father and is in a complicated relationship with Carter (Reversals of Fortune). After returning to the city, Serena can't decide whether she wants to leave for Brown University, and stays with Chuck while she tries to figure it out. But after misunderstanding Chuck's reasoning for telling Rufus, she invites Carter to help ruin Chuck's new business deal, which they accomplish and they begin to casually date (The Freshmen). Serena eventually decides defer Brown, which Lily does not take kindly to. In order to prove she made the right choice, she takes a job as an assistant to publicist K.C. (Dan de Fleurette). At the same time, Chuck is sus about Carter and with the help of Nate's new girlfriend, Bree Buckley, discovers that Carter abandoned her cousin, Beth Buckley, at the altar after proposing to her to get the Buckleys to pay off his gambling debts. He gives him an ultimatum: he either tells Serena himself or he can take a prepaid train ticket and leave for good. At Lily and Rufus' wedding, Carter tells Serena the truth and turns himself into Beth's brothers, who plan to make Carter work off his debt on an oil rig in Texas (Rufus Getting Married). Once Serena discovers where he is headed, she and Nate team up to save him. They attend a poker game held by PJ Buckley, whom Serena convinces to play for Carter's debt in exchange for her offering a photo of Nate's cousin, Tripp van der Bilt, at his bachelor party holding a bong. After they lose the game, Serena overhears a conversation between Nate and his grandfather, William van der Bilt, where she discovers they planned for her to lose all along and trick the Buckleys into releasing a doctored photo of Tripp to hurt their reputation. She tells PJ about the plan, and in return he orders Carter's release. However, Carter is unhappy with this and admits he wanted to go to Texas to punish himself for what he did to Beth and to prove that he is a better man to Serena. He breaks up with her and leaves her heartbroken (Enough About Eve).
After her break up with Carter, Serena works hard with K.C. She agrees to use the client list to invite celebrities to Chuck's new hotel bar opening party, but is angered when Chuck and Blair deliberately call the cops on the party and the clients are photographed leaving the scene. This leads to a new feud between her and Blair (How to Succeed in Bassness). After quitting her job, Serena takes a new job at Tripp's office, where he is running a campaign to be a Congressman for New York and the two begin to develop feelings for each other after Tripp saves a drowning man, winning him the election (The Grandfather: Part II). At Cotillion, Blair and Serena make up after Chuck and Nate intervene (They Shoot Humphreys, Don't They?). Once Nate discovers that Serena and Tripp are growing closer, he tries to keep them apart and realizes he still has feelings for Serena, but she ultimately chooses to be with Tripp after it comes out that his wife, Maureen van der Bilt, set up the man drowning to win him the election (The Last Days of Disco Stick). They enter into a relationship, and after being outed at Thanksgiving, the two leave town together (The Treasure of Serena Madre). After a few days, Tripp secretly meets with Maureen and they agree to stay together publicly but behind closed doors, he can be with Serena. Maureen asks to meet with Serena privately, which Tripp reluctantly relents to. When Maureen explains their arrangement to Serena, she also blackmails her with a letter she stole from the van der Woodsen's from William, who shares that he couldn't see Serena when she came looking for him because he was with Lily. Serena refuses the proposal, insisting Tripp won't agree to the idea. However, she is shocked when he admits that he will to keep his political career, and asks him to take her home. On the way, the two are in a car accident after Tripp swerves to avoid hitting a deer and he leaves the scene after discovering Serena is injured. Meanwhile, Nate, who has recently realized he has feelings for Serena, goes to the hospital where she is being treated. Tripp and Maureen eventually show up, and share that William will provide an alibi for Tripp, relieving him of any involvement of the accident. Nate punches Tripp and tells him to leave, then goes to be with Serena (The Debarted).
After the accident, Serena stays at the Waldorf's and is trying to figure out her relationship with Nate. She is advised by Blair to make him jealous while Nate is advised by Dan to take it slow. The bad advice leaves them to attend the French Ambassador dinner separately, Serena bringing Damien Dalgaard, an old friend, as her date and Nate coming alone but ending up hanging out with Jenny Humphrey. After successfully making the other jealous, they end up together at the end of the night and enter into a relationship (The Hurt Locket).
Elsewhere, Chuck believes he has found his mother, who he spent his whole life believing was deceased. Serena realizes this situation hits close to home, due to her father not being able to see or talk to her and she decides to stop looking and trying to contact him as a result (The Lady Vanished). Meanwhile, Jenny has begun dating Damien but Lily and Rufus try to keep them apart after discovering he is a drug dealer. Serena tries to intervene but fails, accidentally instigating a fight between herself and Nate; however, the two soon make up (The Sixteen Year Old Virgin). Soon after, Jenny is drugged at a Waldorf Designs fashion show and is saved by Nate, leading to her developing feelings for him despite knowing he is with Serena (The Empire Strikes Jack).
On Nate's birthday, Serena plans a special surprise party for him but acts uninterested in celebrating otherwise, to build the suspense. A hurt Nate spends the day with Jenny, who is trying to keep him away from Serena. After they arrive at the party, a game of Assassin begins and eventually culminates in Jenny and Nate as the only two left. Jenny kisses Nate, who shockingly reminds her he is with Serena (Inglourious Bassterds). Afterwards, Carter returns to town and Serena begins to secretly see him and lies to Nate to cover it up. While planning Dorota Kishlovsky and Vanya's wedding, Chuck lets it slip to Nate after a heated argument. Later that day, Jenny confirms it by finding a hotel key to Carter's hotel room in Serena's purse. On the way to the wedding, Nate and Serena argue about whether she can see Carter. Before the ceremony can begin, Carter shows and and tells Serena her father's location in Florida, adding that he has already gotten them plane tickets. Serena hesitantly agrees to go, but discovers in the car that Carter has known for awhile and pretended not to in order to spend more time with her. She kicks him out of the car and attempts to call Nate, but Jenny answers the phone. Serena asks her to explain the situation for her and to also apologize to Nate, which Jenny agrees to but doesn't plan to do. Later that night when she lands in Florida, she arrives at her father's hotel room to discover Lily inside (The Unblairable Lightness of Being).
Not too long after, Serena and Lily return to New York where Lily plans to tell Rufus her secret: that she has cancer and has been seeing William for treatment. However, William beats them to the VDW apartment, surprising Rufus, and all three tell him together. Afterwards, Serena and William begin to bond and build a relationship. Meanwhile, Jenny has been a friend to Nate in Serena's absence, hoping their friendship would become something more. A newly single Chuck helps her with ideas to break Serena and Nate up, which ends in Serena catching Jenny trying to kiss Nate. She stops them in time and Jenny decides to stop pursuing him (Dr. Estrangeloved).
After a few weeks, William announces his plans to move into the VDW building. Serena is very excited, and Lily is okay with the idea knowing it will benefit Serena and Eric. However, Rufus and Jenny have their qualms about it and Rufus uses his new friend, Holland, to deny William's application for a unit. Serena finds out and tells Lily and the two angrily leave to attend the library benefit alone with William. Rufus decides to go to the event anyway and arrives just in time to see William publicly declare his love for Lily. Lily realizes Rufus was right after all, and William is trying to get closer to her and they leave together. At the end of the night, Holland confesses to Serena that she and Rufus slept together, leading Serena to begin to box Rufus out (It's a Dad, Dad, Dad, Dad World). When things come to a head, Serena stands with William while Blair, Dan, Jenny, Nate, and Chuck set out to find the truth, not believing Rufus cheated on Lily. They discover that William and Holland have been working together to keep apart Rufus and Lily, including Holland writing prescriptions for Lily that have side effects that mimic the symptoms of cancer. When confronted, William insists Lily is truly sick and offers to get proof. However, he never returns and the family takes it as an admission of guilt. Serena follows him to where his helicopter is waiting to leave and he admits that Lily was really sick at first but while he treated her, he fell in love with her again and wanted to win her back. Serena tells him that all she ever wanted was for him to be there and while she can't forgive him, she doesn't need to punish him and lets him flee without facing the cops who are on the way (Ex-Husbands and Wives). Afterwards, Serena stays with Dan, and the two fall asleep in his bed. Jenny catches them and sends a pic to Gossip Girl, who posts it. When Nate confronts her about it, Serena asks for some time apart and they break up. She leaves for the summer with Blair to spend in Paris, planning to spend her time working on herself (Last Tango, Then Paris).
During the summer, Serena goes on many dates to distract herself from Dan vs Nate, while Blair keeps to herself until she's invited out by a man she rightfully suspects is a prince from Monaco, Louis Grimaldi. Serena is invited along with Louis' friend, Jean-Michele. Louis has his suspicions that Blair is only going because she believes he is a royal and when they arrive to pick up the girls for the date, Jean-Michele is introduced as the royal. A disappointed Blair also discovers during the date that Serena will be attending Columbia University in the fall as well, leading them to have an argument over Blair having to share her spotlight with Serena yet again. The fight ends with Blair pushing Serena into a fountain outside the restaurant but the two make up at the end of the night (Belles de Jour).
Meanwhile, Chuck is presumed as dead after the Paris police find a body with his identification on him. Serena goes to identify the body but discovers it is not Chuck, but someone who stole his wallet. After some detective work, Serena is able to track him down at an apartment he is living at with the woman who saved him after the mugging, Eva Coupeau. Chuck shares with her his plan to adopt a new identity and life in Europe, disappearing from New York forever. Knowing Blair is the only one who can stop him, Serena convinces her to talk Chuck into coming home. Back home, Nate is dating Juliet Sharp, a woman he met at a restaurant, and she attempts to help him fix his social life. When Serena returns, she is surprised to find them together, as well as Dan being back together with Vanessa Abrams. At the end of Double Identity, the closing scene shows Juliet's apartment is filled with screenshots of Gossip Girl's website, but the main attraction is Serena's mugshot.
When Blair and Serena begin school, they both attempt to gain entry to Hamilton House, a secret society within the student body. Both girls are surprised when Blair is accepted but Serena is not, and Serena begins to suspect that Juliet, they Keyholder of the house, had something to do with it. When confronted, Juliet mentions that Blair called and told them about Serena's involvement in the death of Pete Fairman, which led to her being ousted, and at the same time tries to convince Blair that Serena not being a member is a good thing. At Fashion's Night Out, Blair and Serena stage a fight to expose Juliet's plotting and she is removed as Keyholder while Serena is given admittance. Serena then also moves into the Waldorf penthouse (The Undergraduates).
Meanwhile, Dan is having problems with Vanessa and turns to Serena for advice. After hanging out for awhile, both realize they still have feelings for each other. Nate also confesses he still loves her and Serena goes home, deciding not to talk to either until she decides for good who she wants (Touch of Eva).
While attending school, Serena is constantly late due to a man in the Waldorf building always stealing the cabs she hails. He uses the opportunities to flirt with her, which she rejects. During Goodbye, Columbia, it's revealed that Juliet's vendetta against Serena is on behalf of her incarcerated brother, Ben Donovan, who wants revenge on Serena. In order to move their plan along, Juliet tips off GG that Serena has an STD. This causes Vanessa to feel insecure, knowing Dan has slept with Serena in the past, and she turns to Juliet to help her find the truth. Juliet uses the opportunity to recruit Vanessa into stealing Serena's phone and is able to sneak an email to one of her professors offering sex in exchange for good grades. Afterwards, Juliet slips the phone into Vanessa's purse and Serena realizes Vanessa must have done it, leading everyone to distance themselves from her. Dean Reuther tells her that while she believes she didn't send the email, there is a lot of drama that surrounds her and she needs to tone it down. Serena decides to be nicer to Juliet, believing that she helped expose Vanessa's plot. At the end of the night, the man who steals her cabs strikes up a conversation with her and the two begin hanging out.
In Easy J, Serena admits to having spent the night with Colin, the cab stealer, when questioned by Blair but explains they spent the night talking in lieu of sleeping together. Serena says she refuses to be one of the women he hands off in a cab every morning. But when she arrives to her new class that day, she discovers Colin is her new professor. Despite this, the two decide to continue trying to date after Serena decides to drop the class. However, once Lily discovers the nature of their relationship, she uses some reverse psychology to convince Serena to focus on her future and not on men. Serena then decides to stay in the class but agrees that they can continue hanging out and getting to know each other in a non-romantic way. At the end of the episode, it's revealed that Juliet knows Colin and he gives her money.
Soon after, Serena and Colin find it difficult to continue remaining platonic. Meanwhile, Juliet is still trying to befriend Serena and is excited when Serena confides in her that she has a crush on her professor. Once she discovers that Colin is also going to be attending Blair's birthday party, Serena agrees to let Juliet come as her guest to be her bodyguard to make sure she doesn't get too close to Colin alone. However, Nate offers to go instead once he learns of the dilemma, not wanting to see Juliet since they recently broke up after Nate caught her talking to Ben. Juliet shows up at the party anyway with Colin, and Nate sees them talking secretly together. He confronts Colin and asks if he is Ben, which Colin denies. Afterwards, Colin confronts Juliet about talking to Ben, which Blair and Nate overhear. Blair, having her suspicions about Juliet, misunderstands and goes to warn Serena that Juliet is interested in Colin too. Nate talks to Juliet, and she confesses that Colin is her cousin and she doesn't want people to know because he is a professor and he tells her that Colin is dating Serena. At the end of the night, Serena goes to Colin's home and admits that even though waiting is difficult, she still wants to and they share a kiss; not knowing Juliet had set up cameras to catch them together (War at the Roses). In Juliet Doesn't Live Here Anymore, Vanessa discovers the photos on Juliet's computer and steals them to expose Serena and Colin. Juliet has coffee with Nate, and reveals that she is poor and Colin, being a billionaire, gives her money to live and go to Columbia. Nate agrees to give her a second chance but that is ruined when Vanessa attempts to reveals the photos. Blair and Chuck defend Serena, and the group banish Juliet from Columbia and Manhattan. At the end of the episode, Serena and Colin break up amicably. After they break up, both Dan and Nate declare their love Serena to her, which she ignores.
Serena then ends up in a situation where she needs to choose between Nate and Dan (The Witches of Bushwick). At the same time, the press has heard about Colin and Serena's relationship and Dean Reuther encourages her to leave the university but both Lily and Serena decline the offer. Juliet and Jenny pretend to be Serena and kiss both Nate and Dan, causing both guys to lose interest in her. At the end of the episode, Juliet drugs Serena and emails Dean Reuther saying she indeed wants to take her up on the offer and leave. After being committed involuntarily to the Ostroff Center (Gaslit) after Lily discovers her overdose, caused by Juliet, Serena admits to Dan that he was the one she came to kiss the night she was drugged. While in counseling, Serena tells a counselor through a series of flashbacks that while she was at boarding school, she developed feelings for her professor, Ben, Juliet's brother, but that nothing ever happened between them. Afterwards, Julie confronts Serena at the center and admits that Ben is her brother, and he was sentenced to five years in prison after Serena accused him of raping her. Serena claims she never accused him of anything and Ben was never anything but kind to her, and realizes Lily must have made the claim behind her back when Juliet says she saw the affidavit Serena signed, swearing the accusation was true. Serena confronts Lily, who confesses that she did it to get Serena back into Constance since no private schools would take her after reviewing her records (The Townie).
Meanwhile, Chuck discovers that Lily is planning to sell Bass Industries, and wrongfully assumes it's going to his father's old associate, Russell Thorpe, a Chicago businessman who is newly arrived in town. Chuck and Serena work together to get Lily to stop the sale and get Ben out of prison. Serena brings the affidavit to the Thorpe's party, planning to give it to a journalist in the hopes of exposing Lily. However, Lily convinces Chuck she is doing the right thing for both of them and their plan is thwarted; afterwards, Lily tells Serena that the affidavit can never get out, because if it did she would go to prison (The Kids Are Not Alright).
Ben is released from prison and he and Serena begin hanging out until he reveals his plans to stay with a friend outside the city. Unhappy with this idea, Serena convinces Rufus to let Ben stay at the loft with Dan. Dan is initially unhappy with this, especially with Ben and Serena growing closer, and bands together with Eric and Damien to get Ben rearrested. Their plan works until Damien breaks up with Eric, claiming to have used him to get rid of Ben, and Eric comes clean. Dan then welcomes Ben back to the loft (Panic Roommate). Despite Ben and Serena making their relationship official, they decide to spend Valentine's Day apart. Meanwhile, Blair is jealous of Chuck's budding relationship with Raina Thorpe and mistakingly believes Serena sabotaged her plans after Raina cancelled her interview for W Magazine, which was Blair's idea in the first place to impress the board there. Blair sets up Serena to catch Ben as a cater waiter at Chuck's party, knowing he had lied to Serena that he was a tutor. At the end of the night, Blair apologizes to Serena and she makes up with Ben (It-Girl Happened One Night).
On Eric's birthday, Damien returns to blackmail him for money, since he knows about Lily's perjury. He successfully gets Lily to write him a check but Ben threatens him to get the money back, which Vanessa witnesses (While You Weren't Sleeping). In Empire of the Son, Ben's mother comes to town to visit. She is cold towards Serena, who tries her best to befriend her. Meanwhile, Lily is being sent threats about her crime and it comes to light that Ben's mother stole the affidavit to give to Russell in exchange for him clearing Ben's name. As a result, Lily turns herself in to the authorities and is sentenced to house arrest; Ben and Serena also break up, due to him not forgiving her for everything that has happened.
Soon after, Serena's long lost cousin Charlie Rhodes comes to Manhattan. Her mother, Carol Rhodes, who is visiting Lily with CeCe, is unaware of this until she runs into Charlie and Serena shopping. After Charlie stands up to her about being able to make her own decisions, she decides to let her stay with the VDWs in Manhattan (The Kids Stay in the Picture). Meanwhile, Prince Louis has also come to New York to find Blair but Serena is suspicious she's hooking up with Dan (Petty in Pink). Still jealous, Serena tries to sabotage Blair's new relationship with Louis by sending his disapproving mother, Sophie Grimaldi, a book of Gossip Girl blasts about Blair's many mistakes (The Princesses and the Frog). Blair knows it was her, but decided to let it go because she figured she was still angry about her kiss with Dan. While celebrating Blair's engagement to Louis, Serena realizes Charlie is scheming to make Dan turn her back to her (Shattered Bass). Vanessa, who was also screwed over by Charlie's scheming, teams up with Serena to find what's really going on. In the finale The Wrong Goodbye, Serena finds out Charlie is off her meds but is able to talk her down from anything extreme and tells her that being Serena van der Woodsen isn't all it's cracked up to be. In the end, she decides to spend the summer in Montecito, California, with CeCe.
After getting a job at the beginning of summer, Serena is working on a film set in Los Angeles. While there, she runs into her cousin Charlie (who was revealed to really be a con artist named Ivy Dickens set up by Carol Rhodes) (Yes, Then Zero). After being offered a more permanent position with her boss Jane, Serena plans to stay in LA until she finds out her job is moving back to New York so she plans to return home with Charlie (Beauty and the Feast). When Dan's book Inside is released, Serena is upset when she discovers her character was written to be flighty, irresponsible, and easy. She's also jealous that Blair was made the star of Dan's book over her. At the same time, her job is threatened by the book when she loses a major movie deal over her portrayal in the book (Memoirs of an Invisible Dan). After Serena loses another major deal, this time regarding Dan's book's movie rights, she confesses to him that she always saw him as the love of her life and he decides to give her the rights (The Fasting and the Furious).
However, the deal falls through (I Am Number Nine) and Serena is offered a job by Nate's new boss Diana Payne to blog for their new social media empire The New York Spectator. She begins her own column titled S by S. Meanwhile, Ivy's ex-boyfriend Max Harding arrives in town and runs into Serena, who he begins a relationship with (The Big Sleep No More). Before CeCe's big party, Serena discovers this and confronts both Ivy and Max in front of the whole family. Ivy concocts a huge lie and Max tries to prove her wrong but fails. This causes him and Serena to break up (Rhodes to Perdition).
After Chuck and Blair's car accident (Riding in Town Cars With Boys), Serena tries to help Blair and Louis' struggling relationship by claiming to be in a relationship with Dan to alleviate any rumors of Dan and Blair (The End of the Affair?). The two enter into a fake relationship, although Serena begins to fall for Dan again despite the fact he's in love with Blair. However, Blair and Louis make real amends and she tells Serena her and Dan can stop their fake relationship, but Serena decides to tell Dan they need to keep it up until the wedding (Father and the Bride). At the wedding reception, Serena admits to Dan that she kept the relationship longer than she had to because she was still in love with him (G.G.).
After Blair runs away from her wedding, Dan lies to Serena about where she is in order to save her alone. However, Chuck and Serena track them down, and Serena decides to take the blame for releasing the video that ruined Blair's wedding and marriage (The Backup Dan). Wanting to make Serena and Dan happy, Blair decides to play Cupid upon returning from her honeymoon and sets the two up. But her plan is ruined when she kisses Dan and Serena witnesses (Crazy Cupid Love). To prove her wrong, Blair and Dan try to hang out platonically and it fails. Meanwhile, a dying CeCe is being rushed to the hospital. At the hospital, it's revealed that Ivy is a fraud. After realizing their feelings are real for each other, Serena decides to accept Blair and Dan are going to be together (Cross Rhodes). After CeCe's wake, Serena receives a package from acting Gossip Girl Georgina, along with all the information to make her the new Gossip Girl (The Princess Dowry).
In her first few days as the new Gossip Girl, Serena accidentally ruins Lily and William's plan to trick Ivy out of the inheritance CeCe left (Con-Heir). After being an It Girl for a long time, Serena decides she wants to make her new found cousin Lola Rhodes the next star. But after Lola betrays her, and Serena spends some time out of the spotlight, she realizes it's where she belongs and begins to tear Lola down to build herself back up (It-Girl Happened One Night). After a chain of events, Serena discovers Lola is her sister due to William and Carol having an affair while he was still married to Lily. In turn, Lily sets up Carol to reveal her scheme to the police. Wanting revenge, Lola asks Serena to help her take down Lily but Serena asks her to stay away. On her way out, she steals the card with Serena's Gossip Girl log in to prove she really is her (Despicable B). After Bart is revealed to be alive (Raiders of the Lost Art), Blair becomes involved in helping Chuck help Bart stay. She asks Serena to be her stand in at a meeting with Dan, to play her as they meet with a rep with the program Dan was invited to attend in Rome. At the end of the episode, Blair's diary is leaked as Serena kept it in Gossip Girl servers and it's revealed it was Serena's doing (The Fugitives). Subsequently, Blair kicks Serena out of her penthouse and Serena sleeps with Dan as retaliation and tapes it. Blair breaks up with Dan to get back with Chuck, and Serena sees that and the end of Rufus and Lily's marriage to get back with Dan. However, Dan tells her that after what she did he wants nothing to do with her anymore. She calls Damien and goes on a drug binge while leaving town (The Return of the Ring).
Serena has spent the summer dating Steven Spence, the CEO of a vitamin company, while calling herself Sabrina (in reference to her character in Inside) and claiming to be from Wisconsin. After being missing all summer, Nate, Chuck, Blair, Dan, and Georgina head off to find her. They find her with Steven and after they confront her, she decides to return to Manhattan (Gone Maybe Gone). Steven gets Serena into some adult societies and she's excited to host the Conservancy Gala until she discovers Steven and Nate's new girlfriend Sage Spence are hanging out. They both assume they're being cheated on until it's revealed they're actually father and daughter (High Infidelity). Desperate to build a relationship with Sage, Serena gets her into Blair's Waldorf Designs fashion show. However, desperate to separate Serena and her dad, Sage ruins the show on purpose but fails and Serena and Steven are still inseparable (Dirty Rotten Scandals). Serena and Steven eventually decide to reveal past lovers to one another but find that Steven slept with Lily long before he met Serena. Meanwhile, Serena finds out Dan wrote an expose chapter on her and begs him not to release it (Portrait of a Lady Alexander). While trying to figure out why Steven is acting distant, Serena discovers an engagement ring and realizes he's going to propose. However, Sage releases her sex tape with Dan during Cotillion and Steven ends things with her (Monstrous Ball).
Serena and Dan sleep together in Where the Vile Things Are after he takes her on an outing eerily reminiscent of their first date. After realizing she needs to make amends with everyone, she finally makes up with Blair (Save the Last Chance) and talks with Dan. She asks if he's sure she's the one he wants to be with and her assures her that she was always the one. On Thanksgiving, Dan and Serena host their first dinner together but all ends when Dan releases the mean chapter he wrote on Serena. They break up and Dan is exiled from the UES (It's Really Complicated). In The Revengers, Serena decides to help Blair with her last scheme and then move to Los Angeles permanently. Before she leaves, Dan begs her to stay but she refuses and leaves anyway. But before her plane takes off, she discovers Dan slipped his final chapter into her bag. In the series finale New York, I Love You XOXO, Serena discovers Dan was Gossip Girl all along, but that it was really a blessing in disguise as it made her realize New York is where she belongs. In the time jump, she marries Dan.
Appearance and Style
Serena is famous for her notable natural beauty. She is often admired for looking gorgeous effortlessly; including her voluminous blonde hair, flawless skin, and a tall, striking figure. She often wears sexy, slutty and tight clothes that flatter her body, sequins, and attention-grabbing accessories. Serena is considered, along with her on-again, off-again best friend Blair, one of the most beautiful girls on the Upper East Side. Her style is based off real life model Kate Moss and is meant to be more boho and casual as opposed to Blair's.
Unlike Blair, who is considered to be the show's antiheroine, Serena is considered more to be a traditional heroine. Her motives are rarely selfish and her negative actions are oftentimes generally motivated by a lack of foresight rather than real malice. She's often seen to be friendly and will befriend anyone, such as when she talked to an out of place Dan at the party where they first met. Unlike Blair, Serena is also trusting, which sometimes doesn't work in her favor. Due to watching her mother's many failed marriages, Serena has issues with truly committing to a man and understanding what real love is, but that seemed to disappear when she married Dan. Serena is often noted to be irresponsible, especially when it comes to being places on time or completing tasks as told. As opposed to Blair, who tends to date men with status, Serena doesn't seem to have a type (such as Aaron Rose in season two or Steven Spence in season six).
Relationships (TV Series)
- Dan Humphrey (Husband)
- Lily van der Woodsen (Mother)
- William van der Woodsen (Father)
- Eric van der Woodsen (Brother)
- CeCe Rhodes (Maternal Grandmother)
- Rick Rhodes (Maternal Grandfather)
- Carol Rhodes (Maternal Aunt)
- Scott Rosson (Half-Brother)
- Lola Rhodes (Three-quarters sister)
- Chuck Bass (Adopted brother, former step-brother)
- Rufus Humphrey (Father-in-law)
- Jenny Humphrey (Sister-in-law)
- Alison Humphrey (Mother-in-law)
- Blair Waldorf (Adoptive Sister-in-law)
- Dan Humphrey (Husband)
- Carter Baizen (Ex-Boyfriend)
- Aaron Rose (Ex-Boyfriend)
- Gabriel Edwards (Ex-Boyfriend)
- Tripp van der Bilt (Ex-Boyfriend)
- Nate Archibald (Ex-Boyfriend)
- Colin Forrester (Ex-Boyfriend)
- Ben Donovan (Ex-Boyfriend; inappropriate relationship-turned enemy)
- Max Harding (Ex-Boyfriend)
- Steven Spence (Ex-Boyfriend)
This character has a Photo Gallery!
"You'd really go out with some guy you don't know? -Dan
"Well, you can't be worse than the guys I do know." -Serena, Pilot (1x1)
"You manipulative psycho bitch!" -Much 'I Do' About Nothing (1x18)
"Hey, it's me, Serena. I still don't know if this is your number but I wanted you to know I'm not looking for you anymore. I thought maybe you wanted to know me... but now it's me that doesn't want to know you. I'm done." -The Lady Vanished (3x14)
"I even made a list of pro's and con's. Dan: good shoulder to cry on. Nate: good shoulders." -Double Identity (4x2)
"I'll stay away from Nate and Dan if you stay away from Chuck and Eva. No plotting, no meddling, no Blair Waldorfing." -Touch of Eva (4x4)
"College is just high school with more expensive books." -Goodbye, Columbia (4x5)
"Because I know this may sound crazy or selfish or like I'm living in the past or something. But you were the love of my life, Dan. And I don't know.. I guess I just always thought I was yours too." -The Fasting and the Furious (5x5)
"It's not the secrets that cause the problems, it's the assumptions people make about them." -The End of the Affair? (5x11)
"I love you, Dan Humphrey. Always have, always will." -G.G. (5x13)
"But what he did with that power was write a love letter. Not just to me, but all of us. He made me realize I don't want to run away, that you guys are my family and I belong here." -New York, I Love You XOXO (6x10)
Hobbies & Skills
- Modeling - In Bad News Blair, Serena is invited to model Eleanor Waldorf's clothes. Later on, in Roman Holiday, it's mentioned that she did a print ad for Gap once. In The Serena Also Rises, Serena jumps at the chance to model in Eleanor's fashion show.
- She spent a summer in Italy where her love of Vespas originated.
- She wanted to take a year off school to teach English in South Asia.
- She's been taking birth control pills since she was 15 years old.
- She dated the captain of the swim team at the end of freshman year.
- She was the first person to be on Gossip Girl.
- When she was a little girl, she loved the banana splits at Serendipity.
- She hasn't eaten bread since she was in middle school.
- During her sophomore year of high school, she skipped more classes than she attended.
- When she was 12, she did a print ad for Gap.
- The writer of the show confirmed that Serena would've voted for Donald Trump as president in 2016.