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 a subway ride to Brooklyn with Vanessa for their college friend's backyard party. Jill immediately falls in love with the down-to-earth moms and homemade bread that people actually eat. 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 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.