In this musical adventure, Alvin develops an alter ego after Brittany rejects his offer to the Valentine Ball. In a dream state, he becomes a dashing Don Juan, the Valentine heartbreaker extraordinaire CAPTAIN CHIPMUNK. Brittany is quickly won over and eagerly accepts his offer to the Valentine Ball. Hilarious consequences follow when Alvin wakes up at the dance and realizes he’s not the dashing debonair Captain Chipmunk.