Pilot Audrey and Jeff, the long-time married pair, invite newly engaged Jennifer and Adam to an art opening. But the day before the event, Audrey and Jeff get into an argument about her unused bicycle which has hung on a hook in the couple's apartment for over two years. Their fight causes Adam and Jennifer to question their own decision to get married. Meanwhile, Audrey fixes up Russell with a friend thinking that the right woman can change his mind about married life.
The Birthday Deal Though he's unhappy that Audrey spent more than usual for his birthday party, Jeff wants to stay on her good side to ensure he gets his yearly birthday deal. Though Jeff won't reveal what he gets, Adam decides to bring up the subject to Jennifer and is then worried when Jennifer not only agrees to give him a birthday deal, but announces that she wants to get one in return. Meanwhile, Russell is obsessed with trying to figure out what Jeff's birthday present really is.
The Young & The Restless Jeff can't take his eyes off Russell's latest hot date when they meet her at the diner, much to Audrey's dismay and embarrassment. Later, when Jeff tries to reassure her that he would never go for a younger woman, Audrey tells him that even if he wanted one, he's too old to get one, and the wager ensues. Meanwhile, Jennifer wants to get rid of their bed because Oliver bought it with an ex-girlfriend.
Game On Audrey isn't happy when Jeff fails to respond to her news of a big promotion at work and thinks he's more interested in the outcome of a Knicks game than in her. Jeff tries to make it up to her by inviting her to floor seats at a Knicks game. But, when it comes time to get ready, Audrey can't decide what to wear and Jeff accuses her of caring more about what she looks like than about him. Meanwhile, Adam and Jennifer argue over how their money is spent now that they are engaged and living together.
Kids Russell reconnects with an older woman he disappointed in bed on his 18th birthday. When Russell accidentally runs into Constance, the older woman from his past, he decides he must demonstrate his physical prowess and right his previous wrong.
Hard Day's Night Jeff doesn't know how to tell Audrey that he got "excited" when Jennifer gave him a massage after helping Jennifer move her couch.
Jeff's Wooby Audrey starts to regret that she made Jeff's favorite t-shirts into a quilt when he can't get enough of it. Jeff's constant reminiscing about each t-shirt's significance makes Audrey start to feel like his best times in life may have come before her.