Snuffy is asked to pick up E.Z. O'Malley's cousin Grumpy for their family reunion this afternoon, but upon meeting him, he's too scared to introduce himself. Snuffy soon learns that Grumpy is nice like everyone else, and after sharing his love of skywriting with his similar love for art, the two become friends.
Snuffy is about to go to his first day of school, but he is scared that he hides. Jay Jay, Tracy and Herky have to search all over town to try and find him, and Snuffy is later visited by Old Oscar, who tells him that he was afraid of his first day of school, too.
Herky becomes a famous hero after saving Sam Sticky at Frosty Pines, and suddenly lets it all go to his head. When it comes time to save Sam again, Herky gets stuck himself and soon learns the importance of teamwork.
Old Oscar is excited to hear his old friend Winnie Winger is coming out to visit him, but he believes she's coming to see his famous stunt, the Double-Over-Under-Upside-Down-Loop-de-Loop. Jay Jay helps him practice the move so he's ready, unaware of that Winnie is only here to visit her old frien...
