The Chipettes are looking forward to be spending Valentine's Day with the Chipmunks. Simon and Theodore are also looking forward in spending the day with them, except Alvin. He is afraid of being crushed again due to the fact that a girl he once had a crush on broke his heart on Valentines. In order to rebuild his confidence, Simon makes a tape for Alvin to listen to while he sleeps. Without realizing, the tape hypnotizes Alvin into believing he is a Casanova named Captain Chipmunk while sleepwalking and is finally able to gather up the courage to ask Brittany... although once he awakens, he cannot remember. So, once he finally gathers the courage to ask her, she rejects him, since she has already been invited by the wonderful, dashing, charming Captain Chipmunk. But of course, the special ends with both Alvin and Brittany finally going together and being voted King and Queen Valantine.

When they can't determine when their birthday is, the Chipmunks set out to find their mother, Vinny, who abandoned them as babies.