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Georgina Sparks's prior relationship with Chuck Bass is first inferred from the end of the episode 14 Season 1, "The Blair Bitch Project," whereby Serena turns up at Chuck's apartment to disclose that 'she' (Georgina) is coming back to the Upper East Side. A greater discussion of Georgina's character and her first appearance is in episode 15, "Desperately Seeking Serena," where it is initially assumed that Georgina is in Switzerland. It was alluded that the reason Serena was seeking Chuck's aid was because of he's past affiliation and mutual understanding of what Georgina was capable of. i.e. her influence on bringing out a negative and degenerative side of Serena was what concerned Chuck. It was later revealed that Chuck lost his virginity (in 6th grade) and had a sexual relationship with Georgina in the past. In the season 1 finale Chuck parts way with Georgina by alerting her parents of her whereabouts. In season 3, she returns sharing a room with Blair, much to Blair's dismay. She causes trouble and eventually leaves the upper east side, In the Season 4 finale, Georgina turns up at Chuck's apartment to ask for help because of her parental problems, but she is quickly showed the door. In the 100th Anniversary episode Georgina manages to bait Chuck to confess his feelings for Blair before her wedding ceremony. As Gossip Girl 2.0, she also spends most of Valentine's Day in pushing Chuck to return to his feelings of jealousy for Blair's affections. In Season 6, episode 10 she helps out with Chuck and Blair's wedding.
PersonalitiesChuck Bass and Georgina Sparks demonstrate a mentor and apprentice model from a former sexual relationship. These included traits of, from prior to the Television Series, psychopathic and predatory behaviour towards to both women and men. These categorical behaviours branched into most of their introductory acts. The answer to the question on who is the mentor and apprentice in their relationship is left ambiguous. It was assumed that Georgina was the initiator and instigator in their dynamic due to her fondness to always head towards Chuck in times of dire need.
E.g.) in the Season 3 finale a pregnant Georgina firstly shows up at Chuck's apartment to announce her troubles with the Russian Mob, probably due to her endearment for Chuck's penchant for schemes, but Chuck remains apathetic to her plight. And in Season 2 Georgina is open arms to the presence of Chuck who is visiting her bible camp to seek her recollection of a past event of Serena's. A 'reborned' again Georgina even tries to convert Chuck of his misguided ways, but she was also aware that he sincerely does not want to change his personality. But for the majority of the times both Georgina and Chuck have little interaction with each other. As with the few men that Georgina is attracted towards, she has an inclination to sabotage their concurrent relationships. Most of Georgina's interaction with Chuck during Season 5 is to deliberately revive his possessive persona and affections towards Blair; to which she succeeds.
He and Georgina are arrested for public indecency, after being arrested whilst naked, and the Bass family bailed both of them out.
As a thank you, Georgina's familly gave Chuck a pet monkey which he named Sweetie.
Georgina's first appears in the season one episode "Desperately Seeking Serena" (episode 1x15). However she is mentioned several times in previous episodes by Serena who is receiving inflammatory and defaming gifts from an unknown recipient. It is initially believed by Serena, Lily and Bart that Chuck was the culprit but it was later revealed to be an approaching Georgina to the Upper East Side. Through his own investigations Chuck discloses to Serena that Georgina can not be heading towards the Upper East Side because his sources states that she is dating the Prince of Burgdorf of Switzerland. Sadly, this is proven to be incorrect when Georgina shows up that very same morning at Constance. It is later revealed that Chuck lost his virginity to Georgina in the sixth grade. Between episodes 16, "All About My Brother," and episode 17, "Woman on the Verge," Georgina and Chuck do not have any direct contact which each other, but she is the topic of secret discussions between Chuck and Serena whereby Georgina has Serena held ransomed. Also, despite what Chuck knows of Georgina's past he initially underestimates the lengths that she is willing to ruin Serena's life. But when a drugged fuelled Serena is recovered by NBJC Chuck decides that it is the last straw. In episode 18 "Much "I Do" About Nothing," an 11th hour Chuck manages to call on Georgina's parents to 'recover' their distant daughter before she manages to further her plans for Serena. Unknown to the audience, Georgina's parents dump their daughter at an extreme Bible camp to be re-educated in the ways of morality.
In Season 2 episode 22, "Southern Gentlemen prefer Blondes," Chuck is re-united with Georgina when he seeks the knowledge of an event where Serena first met Gabriel; the later part revealed to be a con. Initially, it is the scheme of both Blair and Chuck to help find the truth from Georgina, but Blair's doubts of Chuck's sincerity becomes an issue and she abandons him at the bible camp where Georgina resides. Georgina is delighted to see that her first guest is Chuck Bass and hugs him accordingly. Chuck is confused with the newly reformed Georgina persona but quickly asks the question on whether she remembers guiding a Serena van der Woodsen to a stranger Gabriela Abrams. She answers that she no recollection of such a meeting and is also aware that Chuck is not here (bible camp) to reform his ways. Georgina seems to have all but given up on her tireless effort to sabotage Serena's life. But whether unintentionally or accidentally, a mere mention of a rendezvous with Blair, ignites Georgina's curiosity. It is unsure to whether Georgina's curiosity stems from a genuine desire for conciliation and forgiveness from Blair or the transference of blame that Blair took part in her 'incarceration.' In either case she decides to return with Chuck in a taxi ride back to the Upper East Side.
In the start of the next episode 23, "The Wrath of Con," a returning Chuck Bass makes plans for his return, but he muses to tempt Georgina back to her old ways with a cheek of words and a flask. While arriving at Chuck's apartment a distressed Georgina is unsure on how well she will be received by Blair, but this is of little concern of Chuck. He is however concerned, given her current state of mind, how the rest of the gang will respond. He tells her that it maybe best for him to gradually re-introduce her presence. Amidst a heated argument on the better methodology to expose Gabriel and Poppy's scheme, an eager Georgina intrusively wishes to acclimate back into the group but receives a less than welcoming reception. Chuck has to admit that her current state is the result of her brainwashing from bible camp.
With Chuck's help they manage to convince this version of Georgina to help in attempting to con Poppy to a transaction and possible arrest. This plan ultimately fails because it lacked the cruelty that required the old Georgina. Chuck also fails to realize that by not supervising her interactions with Blair Waldorf that Blair has marked her as insane and not welcomed to the Upper East Side. This trigger releases a future vendetta towards Blair on ongoing seasons and the aim to destroy her future relationships. In the season 2 finale, "Goodbye Gossip Girl," Georgina enrols at NYU with a specific request for a shared dormitory with Blair.
Between Season 3 episodes 2 & 3 "The Freshmen" and "The Lost Boy," Chuck and Georgina have no interaction with one another, but her presence and success at adapting to the NYU scene has direct implications on Chuck's relationship with Blair. Georgina succeeds in placing doubt in Blair's mind that she is no longer relevant in a place like college to which Chuck counters Georgina's manipulations with a indirect intervention for Blair's insecurities.
In episode 5, "Rufus getting Married," Chuck witnesses Georgina's machinations at work again for Lily and Rufus's wedding. It results in pre-emptively disrupting the wedding service. By the end of the episode it is assumed that Chuck plays a small role in the mission "Ditch the Bitch in Belarus." i.e. using a hook and bait play-book Vanya manages to ditch Georgina in Belarus to fend for herself. It is inferred that in order for Georgina to escape her predicament she begun a relationship with someone in the Russian mob hierarchy. This landed her in trouble off screen.In episode 22, "Last Tango, Then Paris," Georgina's first visit since her hiatus is to Chuck's apartment. Unbeknownst to Chuck the reason for Georgina's appearance is due to her pregnancy and her troubles with running away from the Russian mob. An unsympathetic Chuck just wants Georgina to leave. Thus he handles her way out to the door. This leaves her with no option other than look for her own scheme to solve her problem.
For the most of season four, Chuck and Georgina have no interaction with one another. Despite both being present at the Constance-St. Jude's reunion party in "Shattered Bass" and "The Wrong Goodbye," they do not cross paths or interact.
In the series' hundredth episode, "G.G.," Georgina has returned to the Upper East Side with a plan of vengeance against Blair Waldorf. Georgina blames the sum of all her previous misfortunes since Season 1 on Blair Waldorf. Parallel to Chuck's non-intentional scheme to breakup Blair's wedding, lies Georgina's own plans to actually disrupt the wedding. She first intends to employ Father Calavalli's aid, but he is indisposed thanks to Chuck's intervention.>
>She then takes on matters on her own hand by trying to seduce Prince Louis in private, but is caught by Lily and Rufus. Eventually she succeeds in baiting and planting the idea into a Chuck Bass to 'fight' for Blair before the ceremony. This allows Georgina to make an incriminating footage of Blair's infinitesimal declarations of love for Chuck. The leaked video halts the wedding to which Georgina revels in Blair's misery. But the disruption is short lived and thus the wedding continues. The end of the episode reveals Georgina to be Gossip Girl 2.0.In episode 14, "The Backup Dan," a Gossip Girl source informs Georgina that Blair has run away from her own wedding. But what she does not know is her location and with who she has run away with. Cleverly, she baits Chuck and Co to meet her at Chuck's apartment by sending a fake txt message. However, after learning of Blair's escape, Serena and Chuck try to ditch her, but she follows them to Blair's location. After dropping the video camera she explicitly assumes that Serena is responsible for the leaked video to the GG website.
In episode 17, "Crazy Cupid Love," Georgina again has no direct interaction with Chuck. But she inadvertently plays cupid by leading Dan Humphrey to make out with Blair in Chuck's bedroom and thus takes a picture. She shows this photo evidence as a perverse way of provoking an emotional response from Chuck. But she finally cements his anger when she reveals it was originally Dan that posted the video.By episode 18, "The Princess Dowry," she manages to further utilise Chuck's feelings of jealousy and betrayal to get Blair's annulment breached. Of course, in exchanged for Georgina's scheme of fixing the dowry problems both Blair and Chuck are owed favors to her in the future.
In episode 20, "Salon of the Dead," it is explained that the Chuck's debt to Georgina was to pay in full for Blair's Dowry.
Georgina: No thank you, the Lord cannot enter the body sullied by alcohol. Chuck: That's good, because I prefer to be the one doing the entering. Georgina: To each his own holy water.
Chuck: I sense aspiration, yearning, striving to be accepted. Then I sense this appealing counter note of sincerity ... This is the story of a young girl who is enjoying her first taste of the spoils of dirty oil. It's perfect.