While Brooke sets out to help her mother connect with her many Pat-hungry fans, enviable new couple Cary and Jess show a young gay man and his daddy around New York City. Later, Chase debuts a career-changing video destined to get the whole world talking.

When Cary heads upstate for a romantic getaway with Jess, a chance encounter with an old friend gives him a taste of the future. Back in the city, a newly rich and successful Brooke kicks off her search for the missing link – a boyfriend – by booking four hotties on her mom's show.

In a desperate attempt to land a legit new agent, Cary tries to rebrand himself as an actor-slash-writer. Meanwhile, Brooke, at long last, lands something of her own – and in doing so, connects with someone from her past.

Cary’s day spent researching for his first-ever movie role ends in melodrama, and a women’s panel finds Brooke in way over her head.

Cary starts dating an A-list actor who “doesn’t comment on his sexuality,” while Brooke struggles to uphold the contractual obligations of her own celebrity tryst.

After a busy day, Pat walks in Chase's fashion show, which he doesn't even care about. When chaos unfolds, Brooke and Cary are forced to make a big decision.

While Cary leverages his D-list celebrity status to help pay rent, Brooke scrambles to enjoy the perks of being a manager at a splashy Vogue party.

After making Chase a bad boy backfires spectacularly, Brooke’s course-correct reminds her that doing good is really hard. Meanwhile, Cary attempts to “win” his reunion, and Pat heads to Ohio to reconnect with her former self.

As Pat searches for a way to have difficult conversations with her kids, Cary reaches his breaking point, while Brooke takes a risk.