Joe and Louis have been best friends since they were young kids and now work together at their own company. When Joe tells Louis he was given a relationship ultimatum by his current girlfriend, Ali, Louis convinces Joe to break up with her. However, Joe has a moment of enlightenment and ends up proposing to Ali. Later, Louis accidentally tells Ali about Joe's original break up plan, and Louis then finds himself not only fixing his best friend's relationship, but their friendship as well.
After learning that Joe and Ali's sex life has been lacking and she doesn't cook for him, Louis goes to secretly confront her about it and gets her to change her ways for the sake of his friend. Meanwhile, Wyatt mentions to Joe that his five year sober birthday is coming up, and he's pretty sure that Louis forgot about it. Joe sends a beautiful cake to Wyatt on Louis' behalf, and Wyatt is thrilled. The guys acknowledge that they are pretty good at taking care of one another, even if they don't always like the help.
With some prodding from Louis, Joe goes through a box of Ali's personal affects and finds a racy photo of her with Derek Jeter in Las Vegas. Joe tells Louis that Ali slept with Derek Jeter, which Louis then shares with Wyatt, and he accidentally blurts it out during an intense game of Celebrity between the couples. Ali is furious with Joe for not being able to keep any of their personal secrets from Louis. Joe eventually convinces her that he needs to share information that makes him feel insecure with Louis, and that he'll work on keeping certain things just between the two of them. Meanwhile, Wyatt gets nervous during Celebrity and misses a bunch of questions because Louis is too competitive. Once he and Joe pair up, he relaxes and does much better at the game.
Joe is stuck in the middle after Ali finds out that Louis has a key to Joe's apartment and she does not.
Joe and Louis' financial problems force the partners to ask for their old jobs back. Meanwhile, Joe questions just how platonic Ali's overly friendly kiss with Wyatt really is.
Louis hires Wyatt to fill in as their assistant at the office when Ro-Ro goes on vacation.
Joe is torn as to where he and Ali should socialize when he realizes that he doesn't fit in with her friends and she doesn't fit in with Louis'.
After Louis offers Joe his grandmother's ring to give to Ali as her long-awaited engagement ring, he is shocked when a hurt Wyatt objects.
Joe is torn as to where he and Ali should socialize when he realizes that he doesn’t fit in with her friends and she doesn’t fit in with Louis’s.