For the past two years prior to this short, Oswald's only outfit was his shorts. But in this cartoon, he's wearing shoes for the first time. Therefore, this marks the beginning where he becomes more decent overtime as the stories go.
In the film, Oswald says goodbye to his boss at the pier, and goes on to have a date with someone in some large house. Unfortunate for him, that someone he wants to date happens to be owned by his boss. Therefore, he has to go back working on the ship.
The animation and the gags here are as good as any quality cartoon of its time. Surrealism is also a good element added.
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