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' birthday party, while Jay decides to take a risk and hire Phillips for an important upcoming event.

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.

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. 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.