She cannot hear what they are saying but in fact Dan is only comforting Ms. Carr who is in tears about the slanderous teacher-student relationship rumor.
Monkey, the dog Dan gave to Chuck in order to relieve Chuck's pain over losing Blair may have been the actual key to Chuck's heart. While talking to Eric, Dan admits he wants to spend Valentine's Day with Blair, but says it's just because he needs her help. Dan's first day at NYU reveals Georgina Sparks' return. Milo makes it into a few episodes in season five with Georgina's new husband, Phillip, who seems to be the only one taking care of him while Georgina is Dan's new manager running around NYC.
Dan has an on-again, off-again relationship with Serena van der Woodsen throughout the series, the two have the longest running relationship on the show and serve as each others primary love interest.
He said that the two were bound to break up eventually and that what they did to Vanessa was sick.
Dan runs to Amanda's aid who brushes him off saying that she no longer wants to see him.
He is attractive but he often felt beneath his rich classmates. Dorota has been in a secret relationship with the doorman Vanya. Olivia apologizes to Dan and they embark in a new relationship. It is unknown whether this book is ever published. To his horror, he finds Chuck getting beatened up by men.
After an awkward hesitation, Blair finally has to pull Dan to her and kisses him. I mean all those carbs will take a toll on your body. Dan soon finds out that someone has published his book, Inside. The next day, he is shunned because of Serena's rise to Queen Bee status. Dan announces that Chuck is getting himself into trouble again, but Blair brushes it off, stating that he's merely doing it to get her attention. She begins avoiding Chuck and Louis, who collaborate to find out what was going on with Blair, and find pictures of Dan and Blair together in New York, learning that the only man she's not avoiding is Dan. He, Blair and Serena are the only characters that appear in every episode of the TV series. She tells Serena that she feels as if Louis had "peered into her soul", and now is happy with the decision she had made, believing that Louis is the one for her. Serena intervenes and Dan and Olivia soon manage to make their relationship public.
Serena was joyed at the revelation, stating that Dan through Gossip Girl, wrote her and everyone else a seven year love letter and made her realize that she belongs in the Upper East Side with Dan.
Dan is good friends with Nate Archibald and Blair Waldorf, he is also a frenemy to Georgina Sparks.
Once they both come face-to-face, Dan closes the door and shows himself out, leaving them both alone. Later Georgina visits Blair and promises to get her rid of her dowry in exchange for Blair's support. Soon afterwards, Serena, Nate, Chuck, Louis's mother, Eleanor and Cyrus all know about Blair's pregnancy, and she decides not to keep anymore secrets regarding her unborn child.