Penny and Aaron end up at Steven's office at the same time, and Penny, in an effort to avoid Aaron, hides under the table. Penny and Randall meet Serena, who tells them she'll be starring in a new musical, Jeremy's Fort. Steven and Cameron attend the Iron Dog opening night in New York, which turns out to be a disaster due to the new director.

Iron Dog's New York opening night has received terrible reviews. Tim, Randall and Gail assist Nolan in auditions for his play, based on Nolan's "Compass-ition" theories. Penny and Raina go to an acting class where Serena is also present, and Serena is bereft due to the bad reviews. Penny and Tim attend an office promotion party for Steven, which Aaron also attends. Penny and Aaron, who realize neither one has seen the reviews yet, leave the party so they can finally read them.

Nolan continues with his unorthodox audition process. Tim, inspired by Nolan's physical prowess, invites Penny and Raina to a fitness class. Penny auditions to play Serena's crippled sister for Jeremy's Fort, and Penny's stiffness from the exercise helps her nail the part. Aaron tells Penny that Iron Dog is closing, and that he's still attracted to her. Nolan massages Tim due to Tim's own stiffness, and Tim discovers that there is romantic chemistry between the two.

Penny gets a callback for Jeremy's Fort, but is unsure whether to go or not, due to the love triangle that now exists between her, Aaron and Serena. Tim realizes that he is attracted to Nolan, but doesn't know whether to make his feelings known. Penny is convinced by her friends and family to attend the callbacks. Gail, aware of Tim's feelings, makes up a reason for Nolan to see Tim again before he is set to leave New York; Tim confesses his feelings, and Nolan reciprocates, although Nolan then has to leave. Penny gets cast in Jeremy's Fort. Penny goes to see Iron Dog on one of its last nights, and tells Aaron afterward that she is still attracted to him as well; the two kiss, but decide to keep any relationship on hold until the end of the run for Jeremy's Fort.

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.

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.

The reading for Vincent Savio's musical, Light Me Up, leads to an unexpected reconciliation. Aaron crashes Steven and Cameron's engagement party to tell her something that will change both of their plans for the future.