Married couple Jeff and Audrey have just learned their next door neighbor, Jennifer, has become engaged to her boyfriend, Adam. But when Jeff tries to give Adam advice, he develops doubt about the impending engagement. Meanwhile, Jennifer fixes up Adam's best friend, Russell, because she believes the right woman could change his habit of being a serial dater. Meanwhile, Jeff inadvertently starts a fight between Audrey and himself about an old bicycle.

While Russell has a hot new date, Audrey bets Jeff that he can't score a phone number from a younger woman and gives him a night without his wedding ring to try.

Jeff puts Audrey in a bad mood after he fails to respond to the news of her big promotion at work because he is watching his basketball game. Jeff tries to make it up by inviting her to floor seats at a Knicks game. But she can't decide what to wear, which it makes Jeff wonder if she cares more about how she looks than about him. Now that Jennifer and Adam are living together, they have an argument over money.

Russell accidentally bumps into an older woman from his past, Constance. He then decides to show her his physical prowess.

Jeff is in trouble. He doesn't know how to tell Audrey that he got "excited" while Jennifer was giving him a massage to thank him for helping her move a couch. Now, Jeff must face Audrey.

Audrey is scared by Jeff's constant reminiscing about each t-shirt's significance. After a little while, she starts to wonder if his best times in life may have come before her.