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. Alhough 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.

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.

Jeff finds himself in trouble when he tries to fix an issue Audrey is having with one of their neighbors.

Barbara returns to town with news that could have Russell very happy.

Jennifer and Adam decide to go on a trip with Jeff and Audrey but may have wished they had stayed home when they find out the reason they took the trip.

Jeff learns a fact about a friend he just met at the gym and Russell has doubts about the family history of a new girlfriend.

After being harrassed for falling asleep during a movie, Jeff tries to prove to Audrey that he's still young by inviting her to his softball game.

Jeff listens to Russell about a co-worker and finds himself in trouble. Timmy is sent to get Russell's phone from the apartment of his most recent conquest.

Adam and Jennifer plan a secret wedding; however, a series of unfortunate events puts their plan in jeopardy. Meanwhile, to keep Russell and Timmy from finding out about the ceremony, Adam tells them he is staging an intervention for Jeff, on the fourth season finale of RULES OF ENGAGEMEN.

Jeff unsuccessfully tries to keep Russell from sleeping with their new surrogate, while Adam tries to work on improving his rear end.

Jeff struggles to figure out how to ask his co-workers to donate money for Audrey's 10K charity run after telling them that he doesn't want to participate in their fundraisers anymore.

When an old photo of Jeff appears in an art gallery, he decides it's time to make some changes in his life. Meanwhile, Russell experiences a slump with women until he sees a familiar face.

Audrey’s throat surgery makes her unable to speak, much to Jeff’s delight. Meanwhile, Russell tells Timmy the only way that he will get a raise is if he does Russell’s dirty work and fires someone.

Jeff discovers that Audrey uses sex to get what she wants, while Russell and Timmy make a commercial for their new soup spoon.

Brenda goes into labor on Jennifer and Adam's wedding day. Meanwhile, Russell and Timmy make an attempt at reconciliation and Audrey surprises Jeff.