Charles Bartholomew "Chuck" Bass is a fictional character in the novel and television series Gossip Girl. In the TV series, he is portrayed by English actor Ed Westwick. Although he is a secondary antagonist in the original book series, the TV series elevates him to an anti-heroic main character, where he is noted for his financial ambition, hedonism and personal style.
Season 1
Chuck grew up on the Upper East Side with his three best friends and fellow elites Nate Archibald, Blair Waldorf, and future-stepsister Serena van der Woodsen. His father is Bart Bass, a self-made billionaire, which is irregular, compared to the Bass' old money friends. Chuck is often described as the "bad boy of his circle." Chuck is a playboy and womanizer who sees women as recreational tools. Chuck frequently skips class and smokes cannabis.  In the pilot episode, Chuck attempts to rape both Serena and Jenny Humphrey. When speaking about Serena in the pilot episode, Chuck says, "Serena looked effin' hot last night. There's something wrong with that level of perfection. It needs to be violated." With time, he attenuates his behaviors as a sexual predator and becomes more of a manipulating womanizer, however, his lecherous attitude continues as he makes multiple advances on his step-sister at the time, Serena.  In episode seven, "Victor/Victrola", Chuck purchases a burlesque club, Victrola. After Nate and Blair break up, Blair visits Chuck at Victrola where she ends up performing on stage. She later loses her virginity to him in the back of his limousine. Though she tries to deny the encounter, Chuck buys a necklace for her and admits that he feels "butterflies" in her presence, leading to a clandestine sexual relationship. Despite this, Nate and Blair rekindle their relationship, leading to a jealous Chuck revealing to the anonymous "Gossip Girl" that Blair and Chuck had a sexual relationship. This leads Chuck to have a temporary rift with both Blair and Nate.  As Bart Bass and Lily van der Woodsen's relationship progresses, they decide to move their families in together. Chuck and Eric van der Woodsen, Lily's son and Serena's younger brother, become especially close. When Serena begins receiving mysterious packages (pornography in the mail, alcohol delivered to her at school), she automatically blames Chuck. Given the creepy remarks Chuck has made about "bathing together" and "turning that onepiece into a no-piece." Serena is not to blame. Bart subsequently forces Chuck to move out of the family home. Serena discovers that the culprit was actually Georgina Sparks, a past classmate of both Serena and Chuck. It is later revealed that Chuck lost his virginity to Georgina in the sixth grade. Chuck and Blair join together to prevent Georgina from further harming and embarrassing Serena. This process rekindles their bond, and they succeed in getting rid of Georgina.  At Bart and Lily's wedding at the end of Season 1, Chuck apologizes and confesses to Nate that he was in love with Blair. During the wedding reception, Chuck gives a speech about forgiveness that is implied to be directed towards Blair. She accepts his apology and the two kiss. However, as they are about to embark on a trip to Tuscany together, Chuck gets cold feet. Blair leaves for Tuscany without him, as Chuck has decided to seduce Amelia, tossing the roses for Blair in the trash can.

Q: How does Season 1 start off?
A: In the pilot episode, Chuck attempts to rape both Serena and Jenny Humphrey.
Who are Serena and Jenny Humphrey?
his step-sister at the time, Serena.
his step-sister at the time, Serena.