"The world you're looking for only exists from the outside. The only reason I survive in it is because I always knew it was empty."
-Chuck to Jenny, Last Tango, Then Paris
Chuck and Jenny initially meet at Blair Waldorf's Kiss on the Lips party. Chuck is instantly drawn to her and asks her to go somewhere private with him to talk. However, he tries to force himself on her but his stopped when Dan Humphrey arrives to rescue Jenny. He punches Chuck and leaves with Jenny before anything happens.
In Seder Anything, Jenny tells Chuck that she never did tell Rufus Humphrey about what he did to her but if she did, Lily van der Woodsen would choose her family over Chuck. After thinking this over, Chuck apologizes to Jenny for what he did and says that if the Humphrey's ever moved in, he would make sure he wasn't around.
In Dan de Fleurette, Chuck brings Jenny as his date to the premiere of Olivia Burke's new movie, Fleur. Jenny agrees, wanting to send Blair a message that she is ruling Constance her way and Chuck wants to prove to Blair that she isn't irrelevant. In Dr. Estrangeloved, Chuck, knowing Jenny has a huge crush on Nate Archibald, advises her on how to put distance between him and his girlfriend, Serena, so she can date him herself. His tips work until Nate chooses to forgive Serena for icing him out and distances himself from Jenny.
In Last Tango, Then Paris, Jenny sends out a damaging blast about Serena and Dan, hurting their respective relationships. After being shamed by Blair, she goes to The Empire to seek refuge in Nate but finds a lonely Chuck instead. After talking briefly about how alone they both are, Jenny decides to lose her virginity to him. However, once Blair finds out, she banishes Jenny from Manhattan and Chuck from her life.
In The Undergraduates, Chuck tries to gain forgiveness from Lily, Rufus, and Eric van der Woodsen. Lily offers to help with the transition and is able to convince Rufus to give Chuck a chance, but he rescinds this whenEric tells him about the Kiss on the Lips incident. However, Lily tells Rufus that Jenny confided in her about what happened a long time ago and Chuck is a changed person now.
Later, Chuck tries to get revenge on Blair for her ruining his relationship with Eva Coupeau. As retaliation, he invites Jenny back to town under the premise of her having an interview with Tim Gunn to attend Parsons. Once Jenny finds out he set the interview up, she decides to get them both back by revealing that the reason Blair and Chuck broke up was because she slept with Chuck. She sends in a tip to Gossip Girl, which is posted. However, she realizes that she did the wrong thing and she needs to continue staying away from the UES drama if she's ever going to grow up.
- Jenny is the second main character to lose her virginity to Chuck, the first being Blair.