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She later loses her virginity to him in the back of his limousine.
Following flings with numerous females and males, his only serious relationship comes near the end of the series, when he begins dating Blair Waldorf, a self-obsessed, luxury loving teenager.
Chuck is the resident "bad boy" of the Upper East Side, and like Blair, is both vengeful and manipulative; the two often scheme elaborate plans together.
As the show progresses, Chuck develops a softer side, specifically towards Lily, Eric, and Serena, his adoptive mother, brother, and sister.
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.
In the twelfth book in the series, Gossip Girl: It Had To Be You (2007), Chuck is rejected from colleges because of poor grades and is sent to military school by his father.
When next mentioned in Gossip Girl spin-off, The Carlyles (2008), it is stated that Chuck never showed up to military school, and his whereabouts thereafter are unknown.In the novels, Chuck is a relatively minor character, and has a series of flings with male and female characters across the course of the series.He got his name, Chuck Bass, from his signature chuckle in a bass tone, which often sounds like a raspy whisper.Chuck is often described as the "bad boy of his circle." Chuck is a playboy and womanizer who sees women as recreational tools. 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.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.