Blair runs into Olivia and asks how she can impress shallow superficial actors. She explains that she wasn't invited to the cabaret night with her new group of friends. Olivia tells Blair she was invited and asks her to join her.

Serena drops her work off at Trip's office and the two run into each other. Serena points out that things are awkward. He tells her that he will be heading to DC. He brings up their last encounter. Serena says nothing happened, but he says it feels like something did happen. They are about to kiss, but Maureen walks in and tells Trip they need to pack. She asks Serena to help him. Trip tries to say no, but Maureen says Serena won't mind.

Nate calls his mom and tells her not to let his grandfather manipulate her. He tells her that she'll have to tell him her new information later. Serena walks in and asks Nate for his advice. She tells him he is the only one he can talk to since it involves Trip. Serena tells Nate that she is trying to avoid Trip, but she can't help how she feels. Nate tells her she can always count on him.

Olivia gets some clothes from her room and Vanessa asks if she is avoiding her. Olivia says she isn't avoiding her, she has just been busy. Vanessa tells Olivia that she and Dan are going to a concert. Olivia tells her that she and Dan had a previous engagement and Vanessa says she understands.

Jenny takes Damian around the city. Jenny sees a couple of girls from school glaring at them as Damian grabs a toy sailboat. Jenny calls Chuck and complains about Damian. Damian tells Jenny he is done and shows her how he was just using the boats to make a drug deal.

Dan and Olivia meet with the theater group. Blair then arrives and tells Dan she is going to be producing and starring in his new play. Dan asks Olivia why he is blowing off Vanessa to write a Blair Waldorf/Lady Gaga musical. Olivia tells Dan that Vanessa is fine.

Dan calls Nate and asks for advice. Nate tells him that Vanessa and Olivia are both trying to prove to each other who he belongs to and Dan needs to prove to Olivia that he and Vanessa are just friends. Serena laughs at how everyone is seeking Nate's advice. Serena then calls Trip and tells him she can't join him. He says he understands, but asks if she can join him for lunch so he can say goodbye. Serena starts to say yes,but Nate shakes his head no. Serena tells Trip she can't and tells him to have a good trip. Nate tells Serena she did great and he won't let her out of his sight until Trip is gone. Meanwhile, Nate's mom goes to talk to Trip.

Dan tells Vanessa that he has to cancel and says Olivia signed him up for the play earlier that day. He then asks for her help. Dan gathers everyone and assigns them their roles. After Vanessa walks in, Dan announces that she will be the producer. Olivia tells Vanessa they are lucky to have her. Olivia and Vanessa exchange awkward banter and Blair tells Dan he better not ruin her cabaret.