Randall leaves for a six-month job as a cruise ship entertainer. Jeremy's Fort rehearsals are awkward for Penny. Aaron decides to leave the city for a while to decide about his love life.

Raina leaves New York to film a TV pilot in Los Angeles. Tim and Gail struggle to find a replacement for Randall, eventually settling on Agnes. Penny finds out from Serena that Aaron has left the city. A video of the director of Jeremy's Fort insulting the theater's artistic director leaks onto the internet.

Aaron has decided to apply to law schools, which leaves Serena bereft. Tim gets a gift package from Nolan full of inexplicable items. After the director is fired from Jeremy's Fort, Linda Avery is hired to take his place.

An unexpected visit from Nolan leads both Tim and Nolan, and Steven and Cameron, to reassess their relationships. Penny unsuccessfully looks for a roommate. A "game night" at Serena's apartment turns awkward for Penny.

Penny has found new roommates. Penny and Aaron have a chance encounter. Gail saves Tim during a challenging meeting with Vincent Savio.

Gail has decided to become a real casting director, and Tim and Agnes put her through her paces. Serena invites Penny, the show's assistant director Josh, and Aaron to a "double date" at a piano bar to promote Jeremy's Fort, but the night ends on a sour note.

A month after their falling out, Serena and Penny remain not on speaking terms, though Jeremy's Fort is a success. Gail manages to steer Vincent Savio toward auditioning talented performers, despite his unorthodox requests. Penny and Aaron have a chance meeting, where Aaron delivers sad news.