Dragon has a toothache and decides to have the tooth pulled only after hearing Jane’s tooth fairy story. When Gunther steals the Dragon tooth, Dragon discovers there is no tooth fairy. Jane sets out to rebuild Dragon’s wounded pride and their unique friendship.

Jester’s hysterical impression of Sir Ivon leads to a face-saving duel between the two foes. Jane is mortified, Jester is terrified and Jane's efforts to save her friend from public doom seem, well, doomed! Luckily, Jester discovers that he can choose the weapon…

Jester is the King’s best hope for winning the inter-kingdom competition of song. However, Jane’s overenthusiastic coaching results in Jester losing his voice. Hope is rekindled when Jane overhears a talented voice but unfortunately she cannot find the singer. Eventually, it turns out that Dragon is the silver throated singer but the problem is that singing is simply not acceptable dragon behaviour.

When the King and Queen are gone for the day on royal business, Jane is entrusted with “protecting the royal heirs”. Unfortunately, babysitting the bratty Prince and playful Princess wreaks havoc on Jane’s plan to study for one of Sir Theodore’s knighthood tests. Jane asks Dragon to keep an eye on the two children but he manages to misplace the Princess in a game of hide n’ seek.

While out on patrol, Dragon's spontaneous loop de loop causes Jane to slip off and free-fall through the air. Dragon manages to save her in the nick of time but is shaken by the experience. He vows that no harm will come to her and becomes something of an overprotective parent. Jane rebels against his suffocating affection and unlocks one of the secrets of her runic sword.

When Sir Theodore assigns Jane the menial task of cleaning his sword, Gunther gloats over getting the easier task of Sentry duty. Dragon accuses Theodore of playing favorites, but Jane defends her mentor... until she discovers a broken sword in Sir Theodore's quarters with mysterious runes on its hilt.