At the start of the show, in black, a ticking can be heard.... It is the sound of one man's mounting anxiety. That man is Jon. He's a promising composer whose agent won't return his calls, who is barely affording the rent on his apartment at the edge of SoHo and who is on the verge of turning thirty ("Thirty/Ninety").

Enter Jon's two friends: Michael, his roommate, who has recently given up acting but is now a successful marketing executive, and Susan, his girlfriend, who is a relatively successful ballet teacher and wants Jon to play "Happy Birthday" on the piano at his own party. Jonathan is fretting about the upcoming workshop of Superbia, the musical that he's been writing for five years, when Susan tries to comfort him, wearing a slinky, sultry, sexy dress ("Green Green Dress").

The next morning, Jon is unable to sleep. Susan then reveals that she wants to leave New York and make a decent life for herself with Jon in Cape Cod, somewhere by the beach. Michael has also been pressuring Jon to come interview at his firm. Jon likes neither option ("Johnny Can't Decide"), but he likes his current job even less – waiting tables at a diner for brunch on a strangely Sondheimian day ("Sunday").

After work, Michael picks Jon up in his new BMW and takes him to see his new Upper East Side apartment. It's still being remodeled, but soon he won't have any of the grime, crowds and bad plumbing that make bohemian life both exasperating and exhilarating ("No More"). Jon finally agrees to interview at Michael's firm.

In the middle of Jon's weekly conversation with his parents from White Plains, his agent finally gets back to him. She is trying to get "interesting people" to come to Jon's workshop. Jon sits down to write when Susan calls, inviting Jon over. He wants to stay home and write, which leads to a fight. Painfully mindful of each other's feelings, Jon and Susan are careful not to step on one another's toes ("Therapy").

On his way to Michael's office the next morning, Jon wanders through Times Square, wondering if his work will ever end up on Broadway. At Michael's office, Jon is asked to participate in a "creative-process-unlocking session" for the naming of a new no-calorie replacement for cooking fat. The process is extenuated, pretentious and more than a little bit painful. Jon, who just wants to name the product already, becomes more and more snide until he manages to get himself kicked out.

Michael is furious at Jon. He doesn't see this as a game or a show to rewrite ("Real Life"). Michael, who is gay, envies Jon for his chance at a marriage, family and normal existence. Jon heads to rehearsal for Superbia, and stops for a pick-me-up ("Sugar"). Caught in the act of buying Twinkies by his show's lead actress, Karessa, he is relieved to discover that she shares his addiction.

Following a successful rehearsal, Jon arrives home to find Susan packing. She has a job offer, teaching "real dancers" in Northampton, Massachusetts. It's for two weeks, but could evolve into something more permanent. Jon doesn't want to stop her from pursuing her dreams, but he also doesn't want to let her go ("See Her Smile").

The day of the workshop arrives. Michael and Susan sit in to offer support. Jon's dad, his agent and a composer/lyricist so famous that he cannot be named are also in attendance. The show begins, and Karessa sings her solo; a soaring rock ballad ("Come to Your Senses"). Everyone tells Jon that the reading went wonderfully... but nobody wants to produce the show.

Jon is devastated. He goes to Michael's office to beg for a job, but Michael tells him not to give up. Frustrated, Jon screams that Michael doesn't understand what it's like to be afraid of the future. Michael subsequently reveals that he is HIV-positive. Shocked at this news, Jon runs to Central Park, unable to cope. He thinks about his past with Michael, all of the shows that they did together and of all the fun that they had ("Why?").

He realizes that life is short and writing is the only way that he wants to fill it. Finally, it's the birthday party, and Jon is turning thirty ("Thirty/Ninety – Reprise"). He makes up with Michael and says goodbye to Susan. To cap things off, Stephen Sondheim calls to congratulate Jon on his reading and invites him to lunch. Then the cake comes, and Jon is led to the piano to finally play his anthem for all to hear ("Louder than Words").