100 Days of Summer, Cruel Summer

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.

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.

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.

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.

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.

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.

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.

The cast reveals fun and formerly unseen secrets as they comment on more memorable moments from their 100 days of summer together.