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At the end of another turbulent summer in the Hamptons, Mother Hubbard activates her friend group in the city; Kyle and Amanda head back to the city for a fall filled with uncertainty.
At Whitney's New York party, Andrea plays matchmaker by setting Lindsay up with a hot milkman; Kenny lands in the center of the drama; Kyle opens up to his mom about his marriage.
Danielle and Lindsay confront their drama to see if they can leave the past behind; Kenny's relationship comments spark conflict; Amanda surprises Kyle with an apartment update.
Kenny confronts Andrea about comments made regarding his relationship, which quickly escalates; Lindsay's desire to date is rekindled by a blast from her past; Kyle and Amanda try to navigate the rules of living apart while staying a couple.
Kyle persuades his friends to engage in Loverboy's unusual guerrilla marketing campaign; a conversation between Danielle and Amanda erupts into controversy; Kenny uncovers the truth about his estranged father.
Nick and Yvonne officially tie the knot; a long overdue call from his estranged father forces Kenny to confront his past; Yvonne worries as Lindsay reverts to old dating habits; in a bid to save her marriage, Amanda makes a big change.
Lindsay and Kenny spark an unexpected bond; Kyle gets some advice from Carl; Yvonne and Nick's wedding dinner unravels as underlying tensions erupt at the table.
The crew heads to Connecticut for Lindsay and Kenny's Friendsgiving getaway; an unexpected comment from Whitney upsets the moms in the house; a revelation about Kyle's future sends Amanda over the edge.