Ben and his sister, Juliet, hatch a plan to ruin Serena's life, and they nearly succeed. When Serena finds out what Lily has done, she tells the truth and gets Ben released from prison, and the two start dating. There's no time to unpack the creepy origins, the trauma of being falsely accused and sent to prison, or the fact that his sister drugged her and left her in some random hotel, making her think she'd tried to kill herself.
The two date pretty briefly before it's clear that it can't ever really go anywhere. Serena doesn't see any red flags in a guy who supposedly ditched his girlfriend for her friend she brought on vacation with them, and they start a relationship. It's all a scam, and it's revealed that Poppy had been in on it from the beginning and they planned to use Serena's rich connections to steal some money.
Serena and Tripp start having feelings for each other while she's working on his campaign. Oh, and he's married, so there's that. He tells Serena he'll leave his wife, and they take off together.
His wife catches up to them and proposes that they keep their affair a secret to avoid the public scandal of a divorce. Serena refuses, but Tripp accepts. If that wasn't enough to end things between them, they get into a car accident on their way back to New York, and Tripp ditches an injured and unconscious Serena in the car. In season two, Serena starts dating Aaron Rose son of the far more interesting Cyrus , seemingly for something to do.
He's a super pretentious artist-type who takes pictures of beautiful women and has an endless supply of scarves. The only emotion he shows is mild annoyance when Serena dares to assume that they're exclusive before he decides that they are. There's really not much to say about this relationship, as he basically serves as a bargaining tool for Serena to try to get Dan to admit he still loves her.
Dan and Serena start dating early on in season one. 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. 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. 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.
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. 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. 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.
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.
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. She begins her own column titled S by S.
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. 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. 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. 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 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. 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.
And no, we're not talking about Lonely Boy still not over it. HBO Max has released a new series inspired by the original show and the best-selling books. According to the streaming platform , the program follows "a new generation of New York private school teens being introduced to social surveillance nine years after the original blogger's website went dark.
Hey, Upper East Siders! Soon, it becomes apparent that her It-Girl persona is just an act to get people to like her and give her the attention she craves for. Serena loves being the center of attention and is willing to do everything to stay there.
Whether she's launching a crusade against Gossip Girl or actually becoming Gossip Girl herself, Serena's fears and insecurities always get the best of her. To say Serena and Lily didn't always get along would be an understatement.
They were both terribly immature and often acted without care or concern for the consequences. Lily always hid things from Serena and even manipulated her, thinking she knew what was best for her daughter.
For her part, Serena enjoyed going against her mother's wishes, especially when Lily's deceptions came to light. Their tortuous relationship often puts them at odds with each other. And while it's fair to say that Lily was a pretty terrible mother , Serena was no angel either, which made for an awfully poisonous mother-daughter dynamic. Serena always thought Dan was a better person than he really was. She often saw him as this morally superior overachiever and put him on a pedestal that he definitely didn't deserve, going as far as considering herself lucky that someone like him fell in love with someone like her.
As a result, she held him in higher esteem than any of her other lovers and always came back to him, even after all the terrible things he did to her and she to him. Dan too put Serena above all others except perhaps Blair, who he arguably ranked higher in his own chain of perfection and refused to see her for who she really was , instead preferring the dream version he came up with.
Time and again, the two hurt and mistreated each other, only to get back together out of some desire to recover the romanticized version of their relationship, which they had during their high school years.
The argument of whether Blair and Serena were actual friends is still a hot one. On the one hand, they supported each other when they needed it the most, even going as far as calling themselves sisters.
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