Two years and five months before Schmigadoon: Josh loses a fellowship to a colleague. Melissa offers some options to move forward but Josh just wants to let it go. They argue over the phrase "dog eat dog world" which Melissa thinks is "doggy-dog." Later in the evening, they reconcile.

In Schmigadoon, Doc Lopez closes up the clinic for the night. He sees Melissa taking off her shoes and decides to join her in her "free-spiritedness." He tries to play the Top Three game with her like Josh used to.

They reprise "Suddenly" and begin dancing through the house. Doc Lopez spins Melissa into The Countess who has suddenly appeared in the front room. Doc Lopez introduces them and Melissa realizes they are engaged. Lopez tries to cover his indiscretion with Melissa until The Countess sends him for champagne.

Alone, The Countess tells Melissa she knows Lopez is in love with her. Melissa admits to it and The Countess proposes they get to know each other by taking a drive in the country together.

Carson, Josh, and Emma have a picnic together. While Carson's counting ants, Josh and Emma discuss living in New York and suddenly, Emma kisses Josh. Josh tries to compliment her on how she's raising Carson but she becomes upset and calls an end to the outing.

In town, Mildred sets up a scenario to get the attention of the townsfolk and promote the message that there's a problem in Schmigadoon. This leads to her pitch to be the town's next mayor.

In the schoolhouse, Emma orders Carson to write lines 500 times. Josh shows Carson how to write two lines at one time.

The Countess is driving Melissa out to the countryside when she reveals that men constantly leave her for "the help". After her song, she forces Melissa out of the car at gunpoint. She throws Melissa's backpack at her and drives away.

In the schoolhouse, Josh approached Emma and she reveals that she is Carson's mother, not his sister. Josh accepts the truth but Carson overhears and is angry at being lied to. He runs away.

Stranded in the country, Melissa finds her heart stone in the things that have fallen out of her backpack and comments she might've been the problem all along.

The lighting changes and a dancer wearing the same dress as Melissa approaches. Melissa identifies it as a dream ballet and refuses to include it.

Josh looks through the woods for Carson and runs into Danny Bailey instead. Danny knocks him to the ground where he finds the heart stone with his name on it that Melissa threw away when they first broke up.