OverviewCherena started before the TV series begun with Chuck and Serena knowing each other since sophomore. In Season 1, Chuck tried to sexually assault Serena at a party. Since that night, Chuck and Serena stayed away from each other, but Serena obviously has forgiven him. Their relationship drastically changes in the second half of Season 1 when Bart Bass and Lily van der Woodsen (at the time) got married, thus forcing both Serena and Chuck to get along with each other as step-siblings. 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.
After many seasons, Chuck plays an integral role as Serena's enabler & mentor during her high school, romantic & College choices, and schemes. Serena plays a great role as Chuck's step-sister; often confiding and giving Chuck guidance during his hardships.
In the books, Serena and Chuck hook up for 3 weeks until gossip girl finds out and creates an eblast and Nate finds out.
Throughout the first couple of Seasons both Serena and Chuck have minimal interaction with one another. Often Chuck plays sexual games and flirts with Serena's affections. Just like Blair, Chuck criticizes and disapproves of Serena's relationship with Dan Humphrey who he views, not only as an Outsider, but someone that has intentionally hurt him. 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). Serena has demonstrated an almost unilateral support, except for the few times with Louis, for Chuck and Blair to get together in a relationship. In concurrence, Chuck seems to easily display his inner passions and thoughts to Serena without any repercussion or judgement; mainly due to their platonic nature. As the series progresses, Chuck and Serena share a very close relationship and often confide in each other. They enjoy spending time together along with their best friends, Blair and Nate. They both care deeply for each other and consider each other family.
Season OneIn Season 1, Chuck tried to sexually assault Serena. This was due, at the time, of Chuck's predatory and innate abandonment issues from a result of his fractured family. 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. 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. Both Serena and Chuck are forced to act on their best behaviors during a party by their respective sole parents for family reconciliation and investors of Bass Industries respectively. However, Serena previously and co-currently at the time kept receiving cryptic and threatening gifts who she blamed for Chuck as the culprit. 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 2, the recurring theme is getting into first-placement Ivy league Colleges. And with the continuous on and off again animosity between Serena and Blair's friendship, Chuck favors Blair, by sabotaging Serena's prospects at a Yale entrance party. Of course, Chuck returns the favor for Serena when he hires Amanda Lasher, an exchange 'actor' student, to cause a series of events that lead to Blair being socially de-throned and Serena rising to Queen Bee Status while an added bonus causing Dan to retain his outsider status at school. In There Might be Blood, both Serena and Chuck are chaperones for Jenny who intends to lose her virginity at a party.
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. They manage to detain Gabriel, however he explains that the funds are all in Poppy's possession. 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.
Season ThreeIn the Second episode of the Season, The Freshmen, a reluctant Serena turns up at the front door at Chuck's Empire Hotel. 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. Serena is happy for him that he such aspirations.
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 Double Identity, both Lily and Serena are extremely worried for Chuck's life when investors and Board Members inform them that Chuck has been missing for months. Serena is asked to check if a body in the morgue is actually Chuck Bass at Paris which she identifies as not him. She then informs Blair of Chuck's possible mortal danger until Blair recounts her previous sudden collision with Chuck. Serena then endeavours, with the help of French Police, to locate Chuck before it's too late to default on Bass Industries. When she finds him with a girl called Eva, he implies that he has received amnesia and any arguments for Chuck to return with her fall on deaf ears. Chuck gives Serena, a subtle and honest hint, that the man that got shot probably does not deserve his redemption. When confirming the stolen ring that Chuck was intending to marry Blair with, Serena enables Blair to confront Chuck to return back to the Upper East Side.In Goodbye, Columbia, a nasty rumor on campus that Serena might have a sexually transmitted disease is spreading on the GG blasts, however a reassuring Chuck (elsewhere plotting a scheme against Blair) asks her to either ignore it as there is bound to be other worthy news. During Chuck and Blair mutual hatred for one another, both Nate and Serena create a written cease and desist agreement to cull the loathing.
In The Kids Are Not Alright, Chuck steals away Serena from Dan to plot a collaborative scheme for their own objectives against Lily Humphrey. In Serena's case it was to get Ben Donovan out of jail while Chuck's intention was to reclaim ownership and selling rights of Bass industries. The scheme included Serena impersonating her mother with Lily's ring and passport to obtain leverage from Lily's National and Savings Bank. Amongst the personal possessions, Chuck finds Lily's raunchy artistic pictures, but most importantly the signed affidavit. Despite some explanations from Lily, both Serena and Chuck are vigilant in confronting Lily with their leverage.In Empire of the Son, Lily prematurely hands herself to the police for the sake of her children, because of a leaked affidavit to Russell Thorpe would provide leverage against Chuck. When confronted with a lie from Russell, he consoles, with compassionate but also confused, Serena that he is ashamed that all he's achievements were for a parental figure that ultimately disappointed him.
In the premiere, Yes, Then Zero, Chuck inspires Serena to embrace the wonders of L.A lifestyle (Los Angeles). At the end of the episode, he comments how proud he is that Serena has tried hard to make a mark at her job and in doing so has grown as individual; unbeknownst that Chuck is suffering from emotional fatigue from breaking up with Blair.
In Memoirs of an Invisible Dan, as an observer to Dan's Insider novel being published, Chuck delights in Serena's dismay in her 'other' worldly projection, Sabrina. In The Backup Dan, a missing Mrs. Grimaldi, leads to Chuck in believing that Blair has second guessed her nuptials and wants to reunite with him with a just as worried Serena by his side. Later in the episode, Serena takes the blame for Chuck's sake because she initially believed he was the sender of Blair's wedding confession to Gossip Girl. In the finale, Serena and Chuck get no interaction with one another.
- Chuck: I love this town. I'm going to have to tell my parents the hotel they just bought is serving minors.
- Serena: And if you get a drink, they're also serving pigs.
- Chuck: Ooh, I love it when you talk dirty.
- Serena: You just love when a girl talks to you.
- Chuck: Actually, I prefer them when they're not talking.
- Serena: [sarcastically] Mm. I've missed your witty banter.
- Chuck: Let's catch up. Take our clothes off, stare at each other.
- Serena: How about I just get a bite to eat? I'm drinking on an empty stomach.
- Chuck: I heard you didn't do that anymore.
- Serena: Special occasion.
- Chuck: Well, how about a grilled cheese with truffle oil? You love truffles.
- Serena: Enough to know it's not on the menu.
- Chuck: I'm connected.
- Serena: Only 'cause I'm hungry.
- Serena: Oh my god, this is so good! Thank you!
- Chuck: You know, if you really want to thank me, I've got a few ideas...
- Serena: It's just a sandwich, Chuck.
- -- Pilot.
- Chuck: (to Serena) So I guess it's just you and me. Apparently my room's available.
- -- The Wild Brunch.