Brian considers ending another dead-end relationship with his latest girlfriend. He makes a pact with Adam, his best friend since childhood, that they both break up with their respective girlfriends. But after Brian breaks up with his latest love, Adam chickens out and instead proposes to his girlfriend, Marjorie, whom Brian actually considers his own Miss Right - a secret that he must keep to himself. Meanwhile Dave, who runs a video game business with Brian called Zap Monkey, and his stay-at-home wife of 13 years, Deena, discuss a possible venture into the world of open marriage. Brian's fortysomething sister, Nic, and her younger husband, Angelo, are trying hard to start a family, but something's not right and their efforts to get pregnant experience a setback. Despite all of the challenges these couples face, they can't wait for Brian to join their "club", though they're not exactly sure why.
As Brian tries to put his secret feelings for Marjorie aside, Adam and Dave Greco encourage him to live the ultimate single man's dream by hooking up with two different women in 24 hours. Meanwhile, Marjorie experiences mixed feelings when she sees Brian moving on. Deena Greco thinks about the possibilities of an open marriage when she meets a cute divorced dad at her daughter's school, and in their efforts to have a baby, Nic encourages a reluctant Angelo to go to a clinic.
When things go awry the day Marjorie moves into fiancé Adam's place, she doesn't want to interrupt him from his deposition work, so she calls on Brian for help - forcing the two to take stock of their friendship. Meanwhile, Dave and Brian anxiously await a call from a potential client who could solve their money woes, Nic and Angelo consider their fertility options, and Deena is torn between staying home with her sick child or accepting a date from the cute divorced dad she met at her daughter's school.
It's Saturday and everyone wants something from Brian, but no one can find him. Brian has decided that he would rather spend the day with his new love, Lisa B (Bre Blair). Meanwhile Nicole, hopped up on her fertility hormone treatments, needs her brother to help her and Angelo with a car problem; Deena and Dave expect Brian to play "Barney" at their daughter's birthday party; Adam, stuck planning the wedding, wants him for some guy time; and Marjorie keeps leaving messages on Brian's phone to talk about their relationship.
Brian's apparent interest in his new girlfriend causes Marjorie to unwittingly sabotage the relationship. Dave, who is convinced that Deena is having an affair, turns what was supposed to be a simple golf outing with the guys into a complicated stakeout to catch his wife in the act. Meanwhile, Nicole has told Deena that spouses shouldn't keep secrets from each other, but she's hiding from Angelo that she's taking fertility hormone injections.