They catch up to Eric, who is with Jenny, Blair, and Blair's friends, and escort him back to the facility.Afterwards, they share their first kiss and enter into a relationship.
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.While he's at the hotel, he accidentally collides with Serena; who is attempting to flee after rejecting Chuck Bass' sexual advances.They date briefly twice in the second season and then remain mostly off until season six.In the time jump in the series finale New York, I Love You XOXO Dan and Serena marry.However, the revelation doesn't faze them and they continue their relationship.
Soon after, Serena's grandmother Ce Ce Rhodes comes to town to attend Serena's Cotillion & Debutante Ball.
At the brunch, Blair informs Dan that Serena slept with her boyfriend, Nate Archibald, before she ran away to boarding school.
Upset that Serena isn't as perfect as he always thought she was, Dan decides not to pursue a relationship with her anymore.
However, Serena is not impressed and admits she wishes they had done something more low-key.
They abandon their dinner in favor of going to a bar and playing pool but their date is once again interrupted when they learn Serena's brother, Eric van der Woodsen, has escaped the rehab facility he is staying at after his suicide attempt.
Right after, Dan and Serena agree to go on another date alone.