Ashlee and Chanel meet Casey, a New York City denizen who opens up about past dramas with Erica. Elsewhere, Joey tries to make amends following pool-party shenanigans; the group travels to the Hamptons; and tension boils over at a Shabbat dinner.
Shabbacolypse continues as Erica and Casey finally attempt to hash out their decade-old issues without resolution. Meanwhile, Amanda avoids the drama by escaping to her love nest with Jeff. Ashlee, Joey, Chanel and Casey survey the man selection at brunch, but the cute guys leave them with a bad taste in their mouths. Then, the girls party the day away at an outdoor bash where Ashlee and Joey butt heads over flirtation techniques. Rob comes to Erica’s rescue, but even he cannot curb her partying ways when things get out of hand on their last night, leaving the rest of the girls baffled and concerned.
Amanda takes Chanel out to cheer her up; Chanel thinks Erica's drinking is hurting her relationships with the others, and Casey volunteers to help; Amanda and Joey work on their business; Ashlee goes on a date.
Casey, Ashlee and Joey try to improve the odds of finding a nice Jewish boy by going speed dating, but their already tenuous friendship takes a turn for the worse as friction starts between Ashlee and Joey. Meanwhile Amanda is throwing a white party to help launch the Drink Hanky. The pressure on Chanel to get married intensifies when she goes wedding dress shopping with her little sister, then explodes at the Drink Hanky party when she ends up in a brawl with another party goer.
Chanel seeks wisdom from her rabbi in the wake of a party debacle. In other developments, Erica and Rob's relationship moves to the next level; and Joey and Ashlee fume and feud over behind-the-back gossip.
Joey's father gives her a 90-day deadline to move out of the house, and when Joey goes apartment shopping with Amanda, she realizes just how painful that's going to be. Meanwhile, Chanel is going through a shakeup of her own -- the loss of her baby sister to her husband. Chanel's sister's wedding has finally arrived, and it's a classic Great Neck modern orthodox Jewish affair.
In the epic season finale of Princesses, Chanel searches for Ashlee, while Amanda, Erica, and Joey enjoy an afternoon of drinking and boating. All is good until they get a stunning text message... Ashlee is in the hospital! The formerly tight-knit group is now divided, and the feud between Ashlee and Joey has forced everyone to pick a side. With Amanda and Erica on Team Joey and Casey on Team Ashlee, Chanel feels compelled to fix their broken friendships. In the spirit of the Jewish New Year, she invites all the girls to a Tashlich ceremony to try to resolve their differences.