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.
When it's time to plan a party for Jeff's birthday, everyone gets involved. But Audrey is spending a little too much time on planning the party, which makes Jeff unhappy. Although Jeff won't reveal what he usually gets in the annual birthday deal, Adam brings up the subject with Jennifer and is then worried when Jennifer not only agrees to give him a birthday deal, but announces she wants to get one in return. Meanwhile, Russell is obsessed with trying to figure out what Jeff's birthday present really is.
Audrey bets Jeff that he can't get a phone number from a younger woman and gives him a night without his wedding ring to try.
Jennifer is mad at Adam beacuse thier bed was bought with his ex. Later, Adam feels the same, except that Jennifer, talking about her exs, said "ALL of them".
Russell has a new date, but he lies about his age... big time!
Audrey gets a promotion, but when she tells Jeff, he doesn't seem excited about it, because one of "his" teams lost. Jeff invites her to another game to make things right.
Adam buys a new videogame, and he and Russell can't stop playing it, until Jennifer discuss with Adam about him spending a lot on stuff for himself.
Jennifer and Adam plan a romantic weekend. Jeff and Audrey look into having children. While Russell runs into an older woman from his past, Constance and decides that he want to show her his physical prowess.
Jeff is in trouble. He doesn't knows how to tell Audrey that he got "excited" while Jennifer was giving him a massage for thanking him for helping her move her 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 stars to wonder if his best times in life may have come before her.
Russell thinks he's got the perfect girl when she keeps making sexy comments but he thinks differently when he realizes she's not doing it on purpose.