As the title implies, the story is set to when everybody is a caveman. But while they wear animal hide, they also wear shoes that are rather modern day in style.
Oswald is riding outdoors on a wooden scooter, looking for a girl to date with. He then comes to a house with an escalator resembling a dinosaur with fins. Coming down to him is a girl teddy bear in high heeled pumps. While they walk together for a few seconds, a big badger sneaks from beside, and pounds the teddy bear in the head with a club. But instead of lying unconscious, the teddy bear falls in love with the badger who takes her away. Oswald is quite surprised.
Oswald learns that a girl would adore a guy who bashes her in the head. He then goes around some more to find another date.
When Oswald attempts to pound someone, another guy tricks him not to do so, and therefore uses the trick to pound and win that girl. In another attempt, Oswald manages to pound a lady to adoring him, only to find her unattractive.
Oswald then heads to some fair grounds where a high striker is being featured. Oswald comes to the machine to test his strength. After two failed tries, he sees the badger and the teddy bear come by. When the badger decides to play the machine, Oswald ties a string between the rock on the game's lever and the badger's foot. And as the badger strikes the other end of the lever, that mustelid ends up hitting the bell head first before going fainted. Oswald then pounds the teddy bear in the head with the game's mallet. The teddy bear reverts to her affection for Oswald.