Amy and Jonah get combative to keep their new relationship hidden from their co-workers. Meanwhile, Glenn spirals when he learns Kelly wants to transfer to a new store, and Cheyenne struggles to organize a Cloud 9 carpool.
When an employee costume competition is announced, Amy and Mateo aren't afraid to play dirty to win first prize, a paid day off. Meanwhile, Glenn is preoccupied by Cloud 9's new automatic cart collector, and Garrett is tormented by an annoying Halloween novelty song.
Amy and Dina are both in labor! But while Glenn's manager status gets Dina the royal treatment at a fancy hospital, Amy and Jonah have a far different experience at a cheaper clinic. At the store, Garrett struggles to express his best wishes for the new parents.
Amy faces a nightmare day at work when she learns she doesn't have maternity leave, made worse by Cheyenne and Mateo campaign to change her baby's name. Meanwhile, Jonah and Garrett take on hiring the new seasonal help.
When a new Cloud 9 initiative forces employees to be friendlier to their customers, Amy ends up getting to know Jonah's parents, and learns he hasn't been completely truthful with them. The new policy also inspires Garrett and Dina to find out who can hold a smile longer.
Jonah and Amy take Glenn's tickets to a managers' conference in Chicago so they can enjoy a free night on the town, but their plan hits a few bumps. At the store, Cheyenne helps Mateo damage control after his undocumented status is leaked, and Dina and Garrett struggle at gift-wrapping.