When did Dan and Serena sleep together?

In one of the final episodes of season three, Dan and Serena sleep together and agree not to talk about it because he’s with Vanessa (Jessica Szohr) and Serena’s with Nate (Chace Crawford) before realizing Jenny had taken a photo of them together and sent it to Gossip Girl.

Did Dan really love Serena?

In the first part of the books, he is in love with Serena Van Der Woodsen because of a party he threw at their apartment before he went to boarding school. When Serena returned to the Upper East Side, she was ostracized by her peers, so she made friends with Dan and Jenny.

Do Dan and Serena ever sleep together?

Serena and Dan sleep together for the first time. Finally, Blair is once again devastated by Nate’s actions after Jenny reveals that Nate kissed her by accident thinking she was Serena. Blair has sex with Chuck, Nate’s best friend.

What was the worst thing Dan did to Serena?

Gossip Girl is known for bringing out the “best” in people, and here are some of the worst things Dan and Serena did together over the years. No surprise here, every fan saw this one coming from a Brooklyn mile away.

What was the relationship between Dan and Serena?

Gossip Girl is a show notorious for featuring unwise relationships between privileged characters, and Dan and Serena are perfect examples of this. Dan Humphrey and Serena Van Der Woodsen’s romance on Gossip Girl was one of those excellent TV love stories, built on two terrible people doing terrible things to each other.

What’s the difference between Serena and Dan in Gossip Girl?

Serena comes across as a sweet, caring young lady born into a world of Upper East Side privilege. While Dan’s not anywhere near-poor, he still was born with less opportunity than Serena has, and hasn’t had everything handed to him on a Tiffany spoon.

Why did Serena have a crush on her Shakespeare teacher?

It turns out Serena didn’t sleep with her teacher but only had a crush on him; Lily added in the sleeping together rumor to “save” Serena’s reputation. When Serena introduces Dan to her Shakespeare teacher, Dan develops a crush on the said teacher.