Bridgette and Nelson address their growing concerns over Rafi. Tutu throws a birthday party for Larry. Eliza reconsiders her medical future.

In 2014, Bridgette and Rafi prepare for the realities of parenthood as Bridgette experiences contractions, leading her on a day of self-discovery through the streets of Boston.

Bridgette’s search for her father leads her to Philadelphia and back home again as she loses the key to his whereabouts. Tutu’s decision to leave Larry alone with Joe unexpectedly leads both Bridgette and Tutu on a path to close the door on their pasts.

Bridgette discovers the hidden strings attached to financial assistance. Rafi and Nelson grow closer as they accept the ugly realities of their cohabitation. Tutu’s own housing is at risk with the increased involvement of Joe Jr.

Bridgette throws a bachelor party for Rafi. Nelson celebrates her engagement with her mother and sister, reigniting their unresolved familial tensions. Jackie helps Tutu accept the realities of a life outside of Southie.

Bridgette misses a date after unexpected news at Ally’s birthday dinner sends her spiraling towards a religious rediscovery. Rafi struggles to establish boundaries with Bridgette in their co-parenting arrangement. Tutu and her sister Jackie are left to sort through their memories of the past.

Bridgette gets a taste of the picture-perfect life of the one-percent, spending a luxurious day at a polo match as a blonde, hobnobbing with celebrities, and celebrating her new best friend’s basic bachelorette party.

At a cookout celebrating Eliza’s graduation, Bridgette comes to terms with the unacknowledged racial divide between the two friends while Eliza admits that Bridgette’s disconnect is ultimately what gives their friendship strength.

On the day of Ally’s birthday, three parallel stories reveal the ripple effects of Bridgette’s night out. Feeling neglected by her husband, Ally goes on a mission to obtain a rare Birkin bag. Ida cares for Ally’s children while she struggles to stay connected with her own daughter in Samoa. Elsie and Mindy have to put their own birthday celebration on hold when Ally makes a special request on their night off.

In the style of “The Magnificent Seven,” Bridgette gathers a posse of white hats to challenge the tyrannical rule of the town’s mysterious baron.