They begin dating for the remainder of the first season before breaking up in Much 'I Do' About Nothing.
They date briefly twice in the second season and then remain mostly off until season six.
“They kept the breakup hidden from the crew, which you could never do now. They kept it from everybody which is a testament to how good they are as actors.
Dan and Serena met at a party thrown by Blair Waldorf that Dan was accidentally invited to.
In Pilot, Serena returns to the Upper East Side after spending a year at boarding school.
Dan initially sees her return and upon learning that she's living at The Palace Hotel with her mother, Lily van der Woodsen, decides to try and run into her there.
If [Penn and I] were photographed walking down the street, they didn’t know if it was a paparazzi shot or if it was a shot from the show." The two still managed to keep their personal lives private.When they did break up, the crew didn’t know for months.“The shocking thing was, I found out on the set of the season 2 finale that Blake and Penn had broken up months before,” co-producer and writer Joshua Safran told .They had a brief conversation that led to Dan having a huge crush on Serena.In Pilot, they accidentally run into each other at the The Palace Hotel and upon returning her cell phone; Serena asks Dan on a date.