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When Princess Toadstool got washed ashore while surfing on her vacation in Hawaii, she was helped up by Cutter, a surfer dude. Cutter also noticed Toad, whom he assumed was a weird kid wearing a funny sun hat, due to his small size and Mushroom cap. Toadstool and Cutter surf, swim, windsail, waterski and hanglide together, and the Princess enjoys herself so much, she questions whether she even wants to return home.
As Princess Toadstool gets better at surfing, Cutter tells her that she should enter an upcoming surfing contest. At the same time, Toad spots Kooky in the bushes, and informs Princess Toadstool that the Koopas are probably causing trouble back home. Having to leave on short notice, Princess Toadstool confesses to Cutter that she's the princess of the Mushroom Kingdom and must return home through a drainpipe, but Cutter does not comprehend the concepts of "Mushroom Kingdom" or "drainpipes", or that his surfing student is actually a princess. Toad warns Cutter not to tell anyone in the Real World of this, to which Cutter agrees, probably out of not wanting to be thought of as weird or not fully understanding what has transpired. Princess Toadstool is somewhat sympathetic to Cutter's difficult sitation, and promises one day to return to invite him as a royal guest of the Mushroom Kingdom, as she should make him feel at home there as much as he has welcomed Peach to the United States.
According to the official DiC production outline for this episode, Cutter's original name was Rick.