Jill's husband, Andy, learns that his baby brother Lex has just earned $600 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.

Candace, Brooke and Lex announce to Jill and Andy that after doing some research in Austria, they found out their family are descendants of a Prussian duke named Von Weber and have decided the entire family should restore the "Von" to their name. Brooke and Candace attempt to lure Jill to their side with a trip to an exclusive spa day to show her the kind of perks that come with the Von name. With the deadline for kindergarten applications for Jill's twins looming, she races to hand deliver them by any means necessary.

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 is surprised when she meets a cool mom at a birthday party with whom she thinks she might actually be able to form a friendship. Jill sets up a double date for them and their husbands at the hottest new Japanese restaurant in town, but is horrified when they run into Brooke, Lex and their friends who insist they join them. Not a fan of large group diners, Jill finds herself stuck in her worse nightmare as Brooke forces the table to try the special eleven-course chef’s choice tasting menu with dishes including one long noodle, a leaf with salt and an empty egg shell. Meanwhile, Vanessa babysits Jill’s kids and unintentionally reveals a little too much about some harsh realities of the real world.

Jill takes a never-ending subway ride to Brooklyn with Vanessa for their college friend’s backyard party. Disillusioned by her Upper East Side neighborhood, Jill immediately falls in love with the down-to-earth moms and homemade bread that people actually eat. However, as the day progresses, Jill realizes the grass may not always be greener on the other side.

Jill gets a frantic call from Brooke who is going into labor a day before her scheduled c-section. When the ambulance refuses to take Brooke to the upscale hospital of her choice, Jill is left with only her wits (and the help of Siri) to deliver Brooke’s first naturally-birthed child. Andy and Lex enjoy an ill-timed technology-free afternoon that ends in a job offer, leading Jill to fear they might be getting in too deep with the Von Webers.