Dating a girl with genital herpes
While there, she does a strip dance routine onstage which entrances Chuck.
While taking her home, they have sex causing Blair to lose her virginity to him (Victor Victrola).
In I Will Always Love You, it is revealed that Chuck went off to Deep Springs College in California and returned a changed man and to have dated Blair in Oxford, England for a year.
Chuck also owns a monkey named Sweetie, gifted from Georgina Sparks' family after the Bass' bailed her out of a situation, and he is known to bring Sweetie everywhere with him.
Charles Bartholomew "Chuck" Bass is a main character in the Gossip Girl television adaptation and a recurring character in the series of novels with the same name. Throughout the television series, Chuck has an on-again/off-again relationship with Blair Waldorf. Chuck is generally shown throughout the first two seasons as the group's bad boy, and is frequently manipulative.
Nate admits to Chuck later that seeing Blair happier after their breakup is causing him to miss her.
Chuck's loyalty to Nate Archibald is shown when he stops him from being taken advantage of by Carter Baizen after a Lost Weekend gone wrong (Bad News Blair).
On a constant search to gain Bart's approval, Chuck explores the option for Bass Industries to acquire the club Victrola.
At Bart's annual brunch, he is told by his father that he needs to meet new people and find something to be apart of.
He also outs Serena for sleeping with Nate (The Wild Brunch).
It's also alluded to on several occasions that Chuck could be bisexual, as he attempted being gay more than once.