Acclaimed author Jill Kargman plays a version of herself as she navigates the treacherous and elite ecosystem of New York's Upper East Side, and the uber-wealthy mommy clique inhabiting this fantastically outrageous domain.
Andy makes partner at his firm but feels overshadowed when he learns his brother has just brokered a staggering sale; Jill feels pressured to get her twins into the right kindergarten; Brooke urges Jill to attend a spinning class charity event.
Candace, Brooke and Lex discover they are descended from a Prussian duke named Von Weber, and they want to change their surname. Brooke and Candace take Jill to an exclusive spa to show her the kind of perks that come with being a "Von."
Jill starts stressing over interviews with kindergartens for her twins after she realizes she is the only mom who hasn't heard from any schools yet. Andy tells Jill his mother wants the whole family to attend an interview for a prestigious, invite-only cemetery.
Jill meets a cool mom and thinks she can actually form a friendship with her. She sets up a double date for them and their husbands at a hot Japanese eatery, but the meal leaves a bitter taste when Brooke, Lex and their friends arrive. Meanwhile, Vanessa babysits Jill's children.
Jill takes the subway to Brooklyn with Vanessa to attend their friend's backyard bash, where Jill bonds with the unassuming moms.
Jill receives a frantic call from Brooke, who's going into labor, and Jill must ultimately help her deliver her child. Meanwhile, Andy and Lex take in a technology-free afternoon, resulting in a job offer.
Jill reluctantly throws a party for Brooke to introduce her newborn daughter to everyone. Meanwhile, Candace consumes painkillers and cocktails, sending her on a hazy walk on New York's streets; Andy is overwhelmed by the excessive perks of his new job.
Jill becomes overwhelmed with her duties at home, so Brooke convinces her to hire a caretaker. Meanwhile, Jill helps Brooke plan her big benefit party.
Brooke and her mombot posse launch an investigation into who has been telling hard truths about life to their children. Meanwhile, Jill fibs to Vanessa about attending a pricey charity luncheon, and Andy discovers Lex's shocking secret.
Jill faces a decision between attending a birthday bash or a prom-theme gala. Andy reveals a secret about Lex, and Candace discloses information that could destroy the family's seemingly perfect appearance.
