Jill's husband, Andy, learns that his baby brother Lex has just earned 0 million from a big overseas sale, diminishing Andy's news of making partner at his law firm. Jill starts to feel the pressure to get her twins into the "right" kindergarten. To make matters worse, Jill's sister-in-law, Brooke, pressures her into coming to her spinning class charity event at SoulWheelz benefitting N.A.C.H.O. (New Yorkers Against Childhood Obesity).

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 with a waiting list a mile long. Jill doesn't make the best first impression and must go to great lengths to secure the family's final resting place.

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 needs to rely on her wits after Brooke goes into labor but she cannot make it to her chosen hospital in time.

Jill reluctantly throws Brooke a "sip 'n see" party so everyone can meet her newborn daughter. At the party, Candace enjoys a potent combination of painhuggers and baby-tini cocktails, sending her aimlessly wandering the streets. Andy is overwhelmed by the extravagant perks of his new job. Later, Jill offers Andy a very special kind of virginity.

Brooke takes Jill to a children's museum to observe nannies in their natural habitat and to try to poach a caretaker to take home with her. However, Jill quickly feels useless when her new staff takes care of everything. With her newfound free time, she is pressured into helping Brooke plan her big NACHO benefit party, creating distance between her and Vanessa.

Brooke and her entourage launch an investigation to figure out who has been too honest with their kids about the harsh realities of the world. Jill finds herself lying to Vanessa about attending a charity luncheon. Andy discovers Lex's shocking secret that could destroy the Von Webers.

Jill needs to make a decision between attending a birthday party or a prom-theme gala. Andy reveals a secret about Lex.