Chuck is largely friendless, but is tolerated by the others because of his family's enormous wealth.
He is described as having flamboyant fashion sense, with a penchant for scarves, and has a pet monkey named Sweetie whom he carries around with him everywhere.
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.
She later loses her virginity to him in the back of his limousine.