Original air date: 01/07/2014 Runtime: 43:01 min. This series premiere kicks off with a Chicago summer staple – having a blast yachting on the lake, and basking in what little sun the Windy City gets. Vince and his new girlfriend raise eyebrows on deck with a bit too much PDA. Things get tense when Pascale rubs Ray’s girlfriend Hamidah the wrong way at Phillips’s birthday party, while Jay decides to take a risk and hire Phillips for an important upcoming event.
Original air date: 01/14/2014 Runtime: 43:01 min. Vince and Lonnie throw their annual summer White Party but Pascale refuses to play by the rules. Tara's charity event brings out Chicago's "it crowd" and their furry friends, while Pascale and Hamidah attempt to patch up their differences. Jay makes final preparations for a major real estate development launch party but finds that doing business with friends can be tricky.
Original air date: 01/21/2014 Runtime: 43:01 min. A friendly game of 'never have I ever' brings up unresolved feelings. Tara starts pressuring her boyfriend to settle down and to move in with her. Jay gets word that Phillips may not deliver on his launch party uniforms in time and is confronted by Vince over lost business. Ray and Hamidah try to get their relationship back on track. Pascale tries to bond with Vince’s new girlfriend, but she's torn after hearing a rumor that may put Vince's relationship in jeopardy.
Original air date: 01/28/2014 Runtime: 43:01 min. Jay confronts Phillips about her work for his upcoming launch event. Pascale gets into a major blowout for spreading a dangerous rumor that threatens Vince's relationship. Phillips and Tara leave Pascale to fend for herself in the aftermath of the fight.
Original air date: 02/04/2014 Runtime: 43:01 min. Jay puts the final touches on his company's launch party. After her spat with Jessica, Pascale is ignored as Phillips and Tara side with Vince. Jay sticks by Pascale while questioning the motives behind her alienation from the group. When Vince tries to make amends, Pascale shuts him down, but her confrontation with Phillips leaves Pascale feeling betrayed. Ray and Hamidah are starting to get back on track when an unexpected family tragedy blindsides them.
Original air date: 02/11/2014 Runtime: 43:01 min. After his mother's funeral, Ray bonds with Vince and Lonnie over a lighthearted round of golf. While Pascale finds success with her jewelry line, Jay tries to find the perfect surrogate for his baby plan. Tara is forced to make a decision about her future with her boyfriend when she finds out Vince and his girlfriend are moving in together.
Original air date: 02/18/2014 Runtime: 43:01 min. As the summer comes to an end, Tara invites the group to her family cabin in Wisconsin for what is supposed to be a relaxing weekend. But after Vince angered Ray by not attending a charity event in memory of his mother, road trip rage and a confrontational dinner threaten to end their friendship. Phillips skips the trip to focus on an important photo shoot for the launch of her doggie clothing line.