It’s a beautiful summer day in Paw Paw, Michigan, and all the neighborhood kids are on their way to Edwina Spoonapple’s house. Edwina, creator and star of The Dear Edwina Show, anxiously awaits her cast and crew as they introduce themselves to us (“Paw Paw, Michigan”). Finally, the kids arrive at Edwina’s, ready to start the weekly episode of The Dear Edwina Show, where folk from around the world send letters to Edwina Spoonapple in hopes of receiving her invaluable advice.
Today, Edwina is especially excited and even more bossy than usual; the talent scout from the Kalamazoo Advice-a-Palooza Festival (the biggest advice-giving convention ever!) will see the show… and their act might have a chance to fill in the slot abandoned by Dr. Joyce Brothers! Alas, right before showtime, one of Edwina’s cast members breaks his leg. Who will fill in for this all-important episode? Bobby, the new neighbor next-door, arrives with brownies from his mom. Edwina. After introducing her siblings, who are playing the drums and piano, Edwina instantly drafts him to perform; Bobby, however, is immobilized by stage fright.
A crestfallen Edwina tells Bobby about the wonderful accomplishments of her three siblings and of their ribbons or report cards tacked up on her parents’ fridge. Her talent, however, has no tangible award… except for the chance to go to Kalamazoo Advice-a-Palooza Festival (“Up on the Fridge”). Bobby is convinced. He joins the show.
The show begins with the full cast, a wheelbarrow full of letters and “Dear Edwina,” promising with song and dance that their marvelous Edwina can answer any problem posed. The first letter is introduced along with a cast member, Scott’s, bumbling admission to his adoration of Edwina (“Here Comes a Letter”). In “Aphrodite,” the letter-writer explains how her brother is a picky eater; she begs for Edwina’s advice. Edwina invites the rock group, Susie and the Napkins, to explain that it’s not what one eats, but what one says, that allows one to be polite (“Say No, Thank You”).
Becky, cheerleader of the Paw Paw Wildcats, gives “Becky’s Cheer” to remind the talent scout from Kalamazoo Advice-a-Palooza Festival that Edwina is the best. “Another Letter” is sung in preparation to move on. Scott, however, has a special letter that he wants Edwina to read. She chooses a different letter and, in “Abigail,” the letter’s author tells us of the woes concerning her obnoxious brother. Edwina illustrates a solution with the story of her scary Uncle Vladimir from Transylvania in “Frankenguest,” where Frankenguest is just about the rudest guest at a birthday party one could have.
In order to choose the next letter, cast member, Kelli, performs the “Poshkonozovich Dance.” In this next letter/song “Carrie” tells about her monstrous lack of knowledge in setting a dining table. Edwina gives her solution in “Ode to Oneida,” where she explains how to set a table.
With a big bow, the company takes a break from The Dear Edwina Show by the lemonade stand (“Time for Intermission”). Scott again tries to get Edwina to read his special letter, but to no avail. As the company looks for the talent scout, they discover that she’s been sleeping!
All are called back to the second half of The Dear Edwina Show (“Here Come More Letters”). The first letter is from Periwinkle, who is very blue because she must move to a place where no one knows her and she is very shy (“Periwinkle”). Edwina replies with the lesson that anyone can make a person feel welcome in a new and strange place just by saying hello (“Hola, Lola”). Becky tries to wake up the lethargic talent scout with “Becky’s Second Cheer.”
Again, Scott tries to get Edwina to read his special letter, but yet another letter saves her. A steel band has lost all the money it’s raised to go to Jamaica (“Ziggy”). Edwina explains the benefits of resisting the temptation to spend foolhardily and to save, save, save (“Put it in the Piggy”)! The Dear Edwina Show ends… or tries to end (“Thanks for Coming”). Scott insists on reading his own special letter, which is about – what else – a boy who is in love with girl who pays him no mind (“Edwina”). Edwina wants to dismiss his pleas, but the company supports Scott, and Edwina is momentarily swept away as the company gives its audience their second and true farewell (“Thanks for Coming 2)”.
All is interrupted by a call from the talent scout. She wants Scott to perform the National Anthem at the Kalamazoo Advice-a-Palooza Festival. The rest of the company, including Edwina, did not make the festival. Edwina is crushed, despite parting words of support from her exiting cast members (“Up on the Fridge – Reprise”). She is interrupted by her little sister, Katie, who has run away from the Summer Math Olympics. It turns out that she has been slighted by her jealous competitors. Edwina gives Katie the advice to be proud and remain herself despite people trying to knock her down (“Sing Your Own Song”). Katie tells Edwina to take her own advice and not let the talent scout knock her down!
Edwina expresses that what really matters is not a prize one can hold, but one’s family, friends and aspirations. Lastly, the whole company sings “Hola, Lola” as an encore for Grandma and her video camera.