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.