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As a result Chuck was banished by Bart away from the family.
When Georgina arrives on the Upper East Side abruptly, Serena confides in Chuck, as he is one of the few people who would understand what she is capable of and explains the drug-overdose incident in her dark past.
In Season 1 both Serena and Chuck often scheme together along with Nate and Blair in a group called the NJBC (The Non Judging Breakfast Club).
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Serena is one of the first people to realize that Chuck has fallen in love with Blair Waldorf after they sleep together at a back of a limo.
When it is revealed that Bart Bass and Lily have been dating, Serena is horrified of the prospect of a future with an accompanying Chuck.
Serena is obligated to behave well for Lily's sake because of her effort for a mother-daughter reconciliation.
Whereas, Chuck is told by Bart to behave for public image as investors are watching their values as a family.
She frankly discusses with Chuck that she is hesitant in attending first year at Brown, because she is unsure if it is the right pathway.
Chuck does not disagrees as he states "For people like us, a College Diploma is just an accessory." In an opened moment, Chuck discusses his future and inner dreams of building an exclusive night club called 'The Vault' in the Empire Hotel for exclusive members with a penchant for debauchery. Their friendship deteriorates when Serena is believed to outed in her life choices to Rufus and reciprocally retaliates by trying and succeeding in collapsing Chuck's prospects with investors for his club.
In Valley Girls, when witnessing Chuck performing a self-less act for getting Blair elected as Prom Queen, she tells Chuck that he deserves to be with Blair.
In the Second episode of the Season, The Freshmen, a reluctant Serena turns up at the front door at Chuck's Empire Hotel.
This is intensified when Bart and Lily get engaged and eventually married.
While Serena is mortified, Chuck is ironically turned on with a possible 'Cruel Intention' relationship with his step-sister.
In The Wrath of Con, Chuck helps Serena recover a stash of stolen funds from Gabriel who has defrauded many of the Upper East Siders including Rufus Humphrey's life savings.