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Set in 15th-Century Europe, a fictional medieval kingdom is ruled by the devious Queen Aggravain and the mute King Sextimus the Silent. King Sextimus suffers from a curse that can only be reversed "when the mouse devours the hawk." The Minstrel sings of the Princess and the Pea ("Many Moons Ago"), though he knows the true tale because he was there when it happened. The princess in the story is not the first girl tested to see if she is worthy of marrying Prince Dauntless the Drab-she is one of 13 girls. The day the Minstrel arrives, the Queen, alongside her confidante, the Wizard, is testing Princess #12 with an unfair quiz. To the Queen's delight, the princess misses the last question: "What was the middle name of the daughter-in-law of the best friend of the blacksmith who forged the sword that killed the Beast?" and is given a rubber chicken by Sir Studley. The populace of the castle complains about an unjust law levied by Queen Aggravain: "Throughout the land no one may wed, 'till Dauntless shares his wedding bed." However, every petitioning princess is sent away after failing unfair tests devised by the Queen. It seems that no one is good enough to marry Prince Dauntless ("An Opening for A Princess").
The crisis escalates when the leading knight of the realm, Sir Harry, discovers that his girlfriend, Lady Larken, is pregnant. Though Lady Larken says that she will run away so he will never have to face embarrassment and the loss of his station, Sir Harry decides that he will set out to find a princess himself ("In a Little While"). He petitions the Queen who immediately says no, but when Dauntless manages to speak up and beg, she gives in.
The Minstrel tells us that in the original story, the princess arrived at the castle on a stormy night (Many Moons Ago - Reprise), but it is not night at all-and the princess only looked as though she went through a storm. Princess Winnifred the Woebegone, a brash and unrefined princess from the marshlands, was so eager to arrive that she swam the castle moat. She immediately charms Dauntless, Studley, the knights and most of the kingdom ("Shy"). However, she also earns the utter loathing of the evil Queen, who vows to stop her.
The King discovers Larken's pregnancy and pantomimes this to his confidantes, the Minstrel and the Jester. He tells them to not say a word, but they both are more worried about the King letting it slip, because even though he's mute, he can still communicate ("The Minstrel, the Jester, and I"). Later, the Queen, assisted by the Wizard, designs a test for Winnifred based on something they are sure she hasn't got at all-sensitivity. They will place a tiny pea beneath twenty thick downy mattresses. If Winnifred is unable to sleep due to the pea, then she will be sensitive enough to marry Dauntless ("Sensitivity").
Meanwhile, Winnifred tells Dauntless and the ladies in waiting about her home in the swamp ("The Swamps of Home") and meets the King, and they immediately like each other. Then, after spilling a purple vase filled with fresh new baby's breath, Winnifred is caught cleaning the mess by Lady Larken who mistakes her for a chambermaid. Soon Harry gets mad at Larken for her mistake and they get in a fight. Larken vows that she will run far far away where she will never see him again.
The King, the Minstrel and the Jester catch Larken trying to run away, and they try to stop her but in the end decide to help her escape to Normandy ("Normandy"). Later that night, the Queen throws a ball so Winnifred can dance the most exhausting dance in the world, "The Spanish Panic". The Queen hopes that Winnifred will tire herself, but the plan fails. Winnifred is the last one standing as everyone collapses from exhaustion at the dance's climax. She asks Dauntless to try to give her a clue as to what the test might be, but he's not sure. He brings out a huge barbell that one of the princesses was asked to lift, but even he cannot lift it. Winnifred does easily and Dauntless admits that he loves her. Winnifred mentions that her nickname is Fred and Dauntless sings of his love for her as she practices numerous tasks she might have to do for the test, including singing, dancing, wrestling, acting, playing the Minstrel's lute, pantomiming and drinking herself unconscious ("Song of Love").
Act II
Later that night the Queen leads the knights and ladies as they carry the twenty mattresses to Fred's room ("Quiet"), and she catches the Minstrel, the Jester, the King, and Larken (disguised in Dauntless' clothes) running away. The Minstrel tries to protect Larken by saying he was escaping with Larken against her will. The Queen declares that the Minstrel will be banished by daybreak. Fred and Dauntless study for the test, and Fred convinces Larken to fix things with Harry. Larken leaves to find Harry, Dauntless bids Fred goodnight, and now she is left alone. While studying a fairytale, she complains about how other fairy tale princesses had it easy and how she wants to live happily ever after ("Happily Ever After"). King Sextimus has a man to man talk with Dauntless about the birds and the bees completely in pantomime ("Man to Man Talk"). The Jester and Minstrel trick the Wizard into telling them of the test and the Jester reminisces about his father's dancing days ("Very Soft Shoes").
Sir Harry and Lady Larken run into each other and they confess that their love is stronger than ever ("Yesterday I Loved You"). When Fred is finally ready for bed, the Queen brings in various people, including the Nightingale of Samarkand, to sing her to sleep ("Nightingale Lullaby") but Winnifred is kept wide awake. It seems that there is some "lump" under the mattresses that is keeping her from relaxing. She starts counting sheep.
Dauntless dresses in his finest to see Winnifred pass the test, but the Queen tells him to his great disappointment that the test has already happened and what it was. Dauntless is heartbroken until Winnifred drowsily stumbles into the throne room while still counting sheep. Everyone is ecstatic that Winnifred has passed but the Queen insists that Dauntless shouldn't throw himself away on Winnifred. Dauntless has had enough of his mother's attempts to control his life and finally yells, "I told you to shut up!". The curse on King Sextimus is lifted (the "mouse"- Dauntless, has metaphorically devoured the "hawk"- Queen Aggravain). Aggravain discovers that she cannot talk and the King can, so Dauntless and Winnifred are free to be married. The King forces the Queen to hop, skip, and jump around the room to everyone's amusement, and with this, she is forced step down.
Finally the real reason why Winnifred passed the test is revealed. After learning about the test, the King, Minstrel, and Jester stuffed the mattresses full of weapons, jousting equipment, and other sharp items. All the items are removed by the Jester in the finale ("Finale"). After the items are removed Winnifred still has trouble sleeping until Dauntless takes the pea out from under the mattress, when she then falls asleep almost immediately. Everyone, in classic fairy-tale tradition, lives happily ever after.