Erin Gerasimovich

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.

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.

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.

Jill dips her toe back in the work world by visiting the fashion magazine where she used to work. But her excitement at being welcomed back with open arms is short-lived.