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It's the middle ages (sort of); Popeye is working in Bluto's Beanery. Bluto is going to the ball where Princess Olive will choose her mate. Popeye's fairy godpappy appears and it's a reverse Cinderella story, with a car created from a can of spinach.
Popeye and Bluto are running competing penny arcades, trying to bring in customer Wimpy. Of course, he would gladly pay Tuesday for a penny today. And of course, their competing arcades show clips featuring each of them, with well over half of this short thus recycled.
Popeye is heading over to see Olive when he hits a traffic island where a cop is directing traffic; when he gets there, he manages to get more tickets for blowing his horn and parking illegally. The cop rings the bell, and Popeye manages to wreck Olive's apartment by dropping what he's doing, each time he writes a ticket.
Big Chief Ugh-Amugh-Ugh is looking for a squaw. Meanwhile, Popeye and Olive are wrestling with their recalcitrant mule and Olive accidentally lands in the Indian camp. Popeye catches up to her. There's an unfair fight, and Popeye is about to be burned at the stake. He drops his spinach, but it cooks and pops into his mouth.
Popeye and Bluto pick up Olive to celebrate New Year's Eve with them. Popeye brings along her granny out of sympathy.
Popeye is leaving on his sailing ship, much to Olive's chagrin. She ends up accidentally stowing away in a trunk. Popeye discovers her, but she can't stay, because the crew will think she's a jinx. She tries to hide, but this only scares the crew more, because they think the ship's haunted. When she is revealed, the crew comes after her to throw her off, and then turns on captain Popeye.
Olive has a small leak in a pipe; she makes the mistake of calling Wimpy to fix it, and the even bigger mistake of asking Popeye to help her do something until Wimpy can arrive. Meanwhile, Wimpy keeps realizing he's forgotten his tools, his gloves, etc. and going back. Popeye finally eats his spinach and manages some fixes to the system.
Popeye visits the bullfight only because of lovely Senorita Olive. He finds himself accidentally in the toreador box, even though he doesn't want to fight because it's cruelty to animals. Popeye rides the bull like a bronco, then gets tossed around a bit. The bull plants Popeye in the ground and attacks; the crowd turns on Popeye. Olive comes down to help and the bull chases her. The crowd throws vegetables at Popeye, including (fortunately) spinach.
Popeye is having a dream. In it, Bluto interupts his and Olive's flirtations with one another and keeps having the upper hand.