In Season 4, Chuck is reaching the legal age where he can takeover the reins of controlling Bass Industries from his parent guardian, Lily Humphrey. Unfortunately, Rufus lets it known to Chuck that she intends to sell its investors. This leads Chuck to meeting Raina who he mistaken for an assistant. When Raina's father reveals his intention to buy Bass Industries she proposes a friends with benefit pact with him as comfort. This develops into an actual relationship when Chuck has to decide in either compromising between business with pleasure. Over a short time, Chuck starts to feel a type of kindred spirit with Raina and has developed true feelings for her. Their romantic relationship comes to a halt when Chuck has a falling out with Lily. They then develop an impartial and distant friendship while she has moved onwards with Nate Archibald. But compounding this is the reveal of Raina's mother's death and her murderer. In the semi-finale it was actually revealed to be Raina's father who is responsible for the mother's death. Raina left the Upper East Side amicably with Chuck in the Season finale.
PersonalitiesEditIn many ways, Raina and Chuck share similar personality traits and history. Both were raised by a single and influential parents. Their parents were both protective and yet intrusive father-figures that felt the need to mould their children's pathways. Both have experienced the lost of their mothers in their lifetime; although the exact true explanation and nature of their deaths are not revealed until later. They also share a similar level of promiscuity and sexual innuendo with one another. i.e. a type of friends with benefits pact. As a result of their burdening legacies, both have the aimed to follow in the footsteps of their fathers by trying to achieve the same aspirations. In Chuck's case it was to one day match he's father's ambition of setting up a Bass Industries. Raina's direction was to directly follow and intern for her father company at Thorpe Enterprises. During her daily routine Raina can be quite candid to others; this was demonstrated when Chuck felt betrayed by Lily that she thought that he was trying to turn her against her own father. They also share an inhibition to seeing other people while non-officially dating each other. Where they differ in their personalities is that Raina has a devoted sense of loyalty to the idea of family, which Chuck has little faith upon from his personal experiences.
Novel Series Edit
Season 2 Edit
Although there is no direct mention of the Thorpe family this season, in episode 9,"Bonfire of the Vanity", Dan Humphrey investigates the origins of the Bass fortunes. It was revealed that a security guard was killed as the result of Bart Bass's building being burnt. In episode 13, "O Brother, Where Bart Thou?," Bart Bass supposedly 'dies' in a car crash which has direct implications for both Raina and Russell Thorpe entering the Upper East Side in Season 4.
It is revealed in episode 11, "The Townie," that Lily Humphrey intends to sell Bass Industries to foreign and external investors, which was a betrayal of Chuck's trust as she is his sole parental guardian; thus she was suppose to only act as his proxy in the best interest of his legacy. This spurns Chuck in "The Kids Are Not Alright" to either stop the buyers from investing or alternatively finding new allies in purchasing majority stock of Bass Industries. This of course serves to him trying to meet an alleged old family friend of Bart Bass named Russell Thorpe. Unfortunately, he gets stone walled in meeting Russell when he wrongly assumes that Raina Thorpe is Russell's personal assistant and has a grievance with her hindrances. It is later revealed from a direct meeting with Russell that she is in fact the Vice President of Thorpe Enterprises, but Chuck unwillingly gives intelligence to Russell that Bass Industries is in the market of being for sale. When it is revealed during a speech party it becomes clear that Russell wants ownership. In sympathy Raina lets Chuck know that it was her father that let the third party investors know of the discord between the family unit of Chuck and Lily. As a consolation and clemency, she baits him to sleep with her.
In episode 14, "Damien Darko," Chuck is finding it difficult to maintain a separation between pleasure and business in his life. i.e. he aims to get Nate's father fired as a consultant to Thorpe while also maintaining a sexual relationship with Raina. Chuck also tries to romance Raina's affection in an attempt to convince her and her father to not only invest in Bass Industries, but to also maintain it's current stature.In episode 15, "It-Girl Happened One Night", Chuck reveals his true feelings for Raina on Valentine's Day. But first he gives Russell the benefit of the doubt that he sincerely wants to work with Thorpe Enterprises in the restoration process by providing a tour of Bass Industries. In many occasions Russell plays along with her daughter's wish to work alongside with Chuck but his comments deride a sense of pretentious criticism. When Russell's only proviso for his investment is the removal of Lily Humphrey from the board of Bass Industries, he complies, but unintentionally causes friction and resentment between him and Lily to a witnessing Raina at a party to honor her. Raina leaves Chuck in disgust as she views loyalty to family as an important trait. He tries explain the circumstances of his life, such as the loathing of his father, to a disloyal mother, and Uncle leaving him with trust issues. He also states: "You Matter to Me..." but she leaves anyways to a distraught Chuck. In episode 16, "While You Weren't Sleeping," with the help of a reconciled Lily, Chuck gathers the intelligence that allows him to supercede Russell in gathering a representative of investors to re-invest into Bass Industries. With this victory, he wishes to re-conciliate his relationship with Raina, but he unknowingly has not realized that she has started to have feelings for his best friend Nate Archibald. In episode 17, "Empire of the Son," Russell has managed to obtain criminal evidence against Lily Humphrey, thus allowing him the opportunity to black-mail Chuck. This marks the turning point for Raina's trust in her father as it displayed the lengths he was willing to go for vengeance. For the sake of Chuck and her children's expectations (Serena and Eric) Lily voluntarily places herself in police custody. But rather than take defeat Russell convinces Chuck with a story that depicts Bart as the instigator of his wife's death in an intentional fire on a building including a guard that was trying to save her. This burden weighs heavily on Chuck's shoulder and the guilt leaves him to verify the truth of Russell's accusation.
In episode 19, "Petty in Pink," Chuck has accepted that the Raina has moved on with Nate while also reaching a mutual trust with each other as friends. That said, because of the mounting evidence against his father, he wishes to conceal the information from a Raina who wishes to seek her mother. He is even willing to go along with her finding her mother despite knowing that the attempt will fail.
In episode 20, "The Princesses and the Frog," Raina learns the 'truth' from Nate that Chuck was deliberately withholding information of her mother's death and murderer. She thus makes a call to create an alliance that liaisons her family with Jack Bass. Luckily in episode 21, "Shattered Bass," Jack's loyalties this time are in favor for his nephew which leads to the truth and confession that it was Russell who intentionally set the fire that night which was originally only designed to murder Bart Bass. Chuck gives him an ultimatum, either comply with Bart's original idle threat to leave town indefinitely or find himself in jail for life. The reasoning was his belief that Raina deserves the imagery of a good father figure who did not murder his wife out of jealousy and hurt. But as a result of Nate revealing the entire truth to Raina, Russell felt sufficiently betrayed to take Blair Waldorf hostage on top of Chuck's hotel at the end of the episode.
In episode 21, "The Wrong Goodbye," Blair manages to send a speed dial to Chuck to notify Chuck of the urgency to aid her from an intentional fire from Russell. With the help of an accompanying Raina she manages to calm and subvert her father's instincts to follow through with the threat, thus allowing the police to arrest him. With her father arrested Raina feels disillusion with her career path and love life so she feels the need to return home to Chicago. She leaves on good terms with both Chuck and Nate.