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.

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 painkillers 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.