At the opening of the show, Austin Bennett prepares for a date with his girlfriend Catherine, but discovers her cheating on him (“Another Saturday Night in New York”). He tells his brother Jeff, who suggests that the best way to win Catherine back is by pretending not to care. Jeff volunteers to find dates for them and plans a night on the town (“Oh What a Difference”).
Meanwhile, Marcy Fitzwilliams is agonizing over her breakup with a man named Larry. Her friend Diana Bingley, an actuary, suggests some “dating rules” that will determine her ideal rebound time, telling Marcy that the best way to find Mr. Right is by finding Mr. Wrong (“The Actuary Song”). Austin and Jeff end up on a double-date with Marcy and Diana after setting one up on J-Date, despite none of them being Jewish. Diana is impressed with Jeff, but Marcy and Austin don’t share a connection at all. Marcy reveals that she is a photographer, while Austin tells her that he writes greeting cards, but only as a way of supporting his passion for poetry. Austin is unable to explain this without frequently mentioning Catherine, to Marcy’s annoyance (“But I Don’t Want to Talk About Her”). Marcy decides Austin is “perfectly wrong” for her.
Meanwhile, Jeff and Diana attempt to have sex, but Jeff throws his back out. Jeff’s hospitalization gives Marcy a chance to try and continue seeing Austin. Over a conversation at the coffee shop, Marcy equates Austin’s coffee preferences with his rigid lifestyle choices in general, and explains her own free-spirited nature (“Coffee”). Austin tries to call Catherine and win her back with an impromptu poem, which fails, and Marcy agrees to help him write a better one. As Jeff returns from the hospital and continues casually dating Diana, Marcy and Austin continue to work on a poem for Catherine, while fighting over details along the way. A bartender and cocktail waitress muse that their differences make them a perfect couple (“The Perfect Romance”).
After Austin completes the poem, Marcy tells him to wait six months before sending it, but Jeff accidentally mails it out with the bills. Catherine’s negative response ends up in Marcy’s hands before Austin has seen it, and she takes him to a Chinese restaurant that offers free wine, in order to get him drunk enough to break the news to him. A series of humorous conflicts with the waiter at the restaurant result in Austin and Marcy skipping out on their bill and stealing a box of wine from the restaurant. Austin is impressed with himself for standing up for Marcy, and thanks her for his acting out of character (“Because of You”). When they are about to kiss, Marcy stops him and shows him the letter from Catherine. He grows angry, and they have a heated argument, but end up having sex. Meanwhile, Jeff and Diana articulate the nature of their “friends with benefits” relationship (“We’re Just Friends”). The next day, Austin is ecstatic over his night with Marcy, and has fallen in love with her, though Marcy doesn’t know how she feels about what happened. Jeff tells Austin to tell himself that he doesn’t love her. Austin tries, but ends up thinking their relationship might have a future (“Maybe We Just Made Love”). Austin admits his feelings to Marcy, who rejects him, telling him she isn’t ready for true love (“Just Not Now”). Ashamed, Austin goes home, and finds Catherine waiting for him.
On the streets of New York, Marcy meets the bartender and cocktail waitress from her first date with Austin, and tells them what happened. They elaborate on the joys of single-hood, and assure her she’s better off. Marcy agrees at first, but changes her mind after seeing a happy couple on the street (“Alone”). Meanwhile, Diana is with Austin and Jeff in their apartment, where Austin has ordered Chinese food. The delivery man turns out to be the same waiter Austin skipped out on earlier. While Austin and the delivery man are settling the bill in another room, Diana tells Jeff she wants to be exclusive. Jeff responds with fear, spelling out the negative impact that would result if they were to be a real couple (“That’s What’s Gonna Happen”).
After the delivery man leaves, Marcy shows up and tells Austin she loves him despite all his flaws, which she mentions in great detail (“Even Though”). Austin is offended by the “anyway” aspect of her love, and rejects her, telling her Catherine has taken him back. Diana, Jeff, Marcy, and Austin sing separately about the hurt they feel from not being with the ones they love (“But I Do”). Marcy and Diana go back to the bar where they had the first double date to drink and forget. The bartender and cocktail waitress remember them, and they all tell tales of lost love in the past, vowing to give up dating.
Marcy and Diana have a change of heart, and the bartender and cocktail waitress imply that they were trying to make that happen all along (“What Do We Do it For?”). Diana tries to talk to Jeff, but is interrupted by Austin, who is fretting that Catherine doesn’t know how he takes his coffee, despite having dated him for five years. Diana explains to Austin that everyone needs someone to love, and Marcy is his. Jeff also admits that he loves Diana (“Marcy’s Yours”). Austin vows to rid himself of his uptight nature, knowing Marcy will accept him no matter what (“Goodbye”). In the final scene, Austin is trying to write a poem for Marcy, but she arrives before he can finish it. He improvises one, spelling out the ways she is different from him, but saying that rather than loving her “anyway” (as she had said earlier), he loves her “because” (“I Love You Because”).