In the show "Gossip Girl," Dan Randolph Humphrey (Penn Badgley) is the son of Rufus Humphrey (Matthew Settle) and brother of Jenny Humphrey (Taylor Momsen). Dan has a passion for writing. Ever since he was a teen he has had a thing for a member of the Upper East Side elite, Serena Van Der Woodsen (Blake Lively). Serena and Blair Waldorf (Leighton Meester) are really close friends. Although at first Dan does not get along with Blair, he later warms up to her.
Dan ends up sleeping with Serena and starts to freak out when Gossip Girl (the voice of Kristen Bell) posts a picture on her blog which shows Serena buying a pregnancy test. This leads to Dan confessing to Serena that he loves her. Later Serena tells him that she is not pregnant.
Trouble starts to stir when Georgina Sparks (Michelle Trachtenberg) appears on the Upper East Side. She is determined to make Serena's life a living hell. Pretending to be "Sara", Georgina gets to know Dan. Dan and Vanessa Abrams (Jessica Szhor) take her in while under the impression that she is a new girl who does not know her way around the Upper East Side. When Serena tells the truth, Dan is convinced that Georgina is lying. He teams up with Blair and manages to trick Georgina into meeting her parents, ultimately getting her sent to a reform school.
Over the summer Dan goes from being the "Lonely Boy" to being the "Playboy". He occupies himself by dating continuously throughout the entire summer so he can forget about Serena. He can't complete his essay due to emotional distress which leads to him getting fired. After losing his job, Dan returns to Hampton for the annual White Party, where he spots Serena and Nate Archibald (Chace Crawford) kissing passionately. This angers Dan and the two quarrel. But it doesn't last for long because his hypocrisy is soon revealed.
Blair constantly tries to protect Serena after she sees Dan interested in the new girl at school. Dan on the other hand believes that Serena is trying to keep the new girl away from him out of jealousy. Dan, Nate and Chuck Bass (Ed Westwick) have their own friendship triangle that is filled with both trust and distrust. During fights, they use their power to bring the other man down, but when push comes to shove, they have each other's back. One of the main things that affects Dan and Nate's friendship is Serena. They both have feelings for her because she leads both of them on unknowingly.
Later, Georgina shows up again. This time she is pregnant and she claims that Dan is the father. She abruptly leaves New York and leaves Dan alone with the baby, but it turns out to be one of her schemes and she returns to take the baby.
"We're interns. I may not know couture, but I know how to collate."
"You do know that 'powerful woman' is not actually a career, right?"