Meet the Princesses, a group of young women from affluent areas of Long Island who live pampered lifestyles in the comfort of their parents’ homes. In the premiere episode, Chanel enjoys Shabbat dinner with her modern Orthodox family, only to be reminded that her marriage clock is ticking. Ashlee gets a mani-pedi with her father and shops for a dress for her 30th birthday party with Joey, the lone Princess from the South Shore. Amanda enjoys a romantic date with her older boyfriend, Jeff, and tries to keep her mother from tagging along. Erica hosts a pool party for the girls that turns from posh fun to mosh pit mayhem as the drinks flow and the season kicks off in dramatic style.
Ashlee and Chanel travel into the city and meet new Princess Casey, a New York City dweller who is anything but the typical Long Island girl. Joey tries to makes nice with Amanda after the pool party debacle caused by her friend. Casey opens up about her painful past with Erica, but tries to put their issues aside for a group trip to the Hamptons. At Chanel’s Shabbat dinner, Casey’s anger boils over, turning a peaceful Shabbat into a Shabbacolypse!
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.
It's Ashlee’s 30th birthday and all the Princesses are there to help her celebrate Long Island--style -- in a club in a strip mall and a scantily-clad crudité server. Later, Chanel gets an unexpected and unpleasant visit from her ex-boyfriend who is anything but Prince Charming. Ashlee takes Casey, Chanel, and Joey to a weekend away at a Jewish singles camp in Connecticut, but a summer storm threatens to throw their trip off track. Back on Long Island, Amanda and her mom Babs take Erica out to the hottest club on Long Island. With boyfriend Rob waiting at home, Erica isn’t afraid to show her flirty side.
Amanda takes Chanel out on the town to cheer her up after an upsetting confrontation with her ex-boyfriend. After Erica repeatedly flakes on the rest of the Princesses, Chanel decides that her drinking is hurting their relationship. She brings it up to the girls and Casey (of all people!) volunteers to help her snap Erica back to reality, but will Erica ever change? Amanda and Joey avoid the drama by busily working on their businesses while Ashlee enjoys a date with an NCB-Nice Christian Boy.
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 partygoer.
After the Drink Hanky party fiasco, Chanel goes to see her rabbi to get back on track. She survives the challenge of maid-of-honor dress shopping and even walks away with a date. Erica's relationship with Rob takes a giant and unexpected step forward when they go shopping for a home together. Joey and Ashlee's friction turns to feud when Joey discovers that Ashlee has been talking behind her back to the other girls. Joey confronts Ashlee about her behavior and the situation goes from bad to worse.
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.
Amanda satisfies her engagement fever by going ring shopping with little sister Taylor. She has Jeff and his parents over in the hopes of bringing their families closer together, but dinner comes to a screeching halt when Babs disapproves of Jeff’s intentions. Despite the discord between Joey and Ashlee, the girls decide to take an end-of-summer trip to a vineyard, followed by a boat ride on Erica's dad's yacht. In a shocking twist, the day at the vineyard goes from fun to farkakt when Erica decides to bring up the elephant in the room -- the Ashlee/Joey issue. Insults, anger, tears, and drama ensue as one of the girls disappears.
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.