Three couples and three different kinds of relationships - married Jeff and Audrey, engaged Adam and Jennifer plus womanizer Russell and his tormented assistant Timmy.
Audrey discovers that Russell is a closeted fan of Broadway musicals, a fact she promises to keep secret in exchange for free theater tickets. Meanwhile, Adam and Jennifer take dancing lessons in preparation for their wedding, but it becomes very clear that Jennifer can’t dance.
After a long line of female assistants, Russell learns that a having a male assistant can be very advantageous. Meanwhile, after volunteering to read to the elderly, Audrey makes a bet with Jeff that she can commit to finishing a project.
Jeff’s New Friend
Jeff is surprised when Audrey informs him that the new friend he made at the gym is gay. Meanwhile, Russell worries the young woman he’s dating might be his daughter.
Much to Audrey’s dismay, Jeff’s chauvinist father, who expects Audrey to wait on him hand and foot, extends his visit after spraining his ankle. Meanwhile, Russell has a one-night stand with a woman who won’t leave his apartment.
After getting invited to a much cooler party, Jeff and Audrey lie to Jennifer and Adam to get out of a dinner they are hosting. At the same party, Russell’s new assistant Timmy (Adhir Kalyan) tries to keep him on his best behavior after he ticks off party-goer Jerry Rice.
Timmy and Audrey conspire when Timmy tires of Russell’s demands and Audrey wants to dump her incompetent assistant. Meanwhile, Jeff thinks he can help the Giants win by re-creating conditions that led to a previous victory.
Old Timer’s Day
After being teased for falling asleep while watching a movie, Jeff tries to prove to Audrey he’s young and spry and invites her to watch him play softball. While up at bat, a simple sneeze proves he’s older than he thinks.
Frustrated by her colleagues’ constant fawning over their newly pregnant co-worker, Audrey pretends that she is also going to have a baby so that she can receive special treatment, too.
When Jeff, Russell and Adam make a bet to see who can "score" the soonest, the three put their thinking caps on and rise up to the challenge. In the meantime, Russell’s new assistant Timmy is also put into place as a watch guard for Russell. But when a series of unfortunate events begin to unwind, Jeff, Russell and Adam are hung out to dry with minutes to spare, leaving a winner that takes everyone by surprise.
While on a double date with Brad and his partner Jackie, Jeff gets annoyed when Jackie helps himself to his meal. Not wanting to hurt Jackie’s feelings, Audrey demands Jeff keep quiet about the incident. Meanwhile, Russell dates a psychiatrist, and has Timmy pretend he is him during sessions. Elsewhere Adam grows a soul patch.
May Divorce Be With You
After Audrey and Jeff learn that their friend Steve’s marriage is in trouble, Audrey agrees to let Steve stay with her and Jeff. She soon regrets her decision after discovering Steve enjoys giving "inappropriate" hugs.
Audrey convinces Jeff that they should do something fun with the profit he made from the sale of his car. However, she regrets her idea after their extravagant night ends up costing them much more than they expected.
Sex Toy Story
After Jennifer hosts a party, Jeff wonders if he and Audrey are missing out on something in their personal life.