Brittany wishes for Alvin to go to the Valentine's Dance with her, due to the fact she has a very large crush on him. However, Alvin thinks that Brittany will not like him and "dump" him after Valentine's Day due to their past experiences. Theodore and Simon try to help Alvin overcome his fear of asking Brittany to the dance by having him listen to a tape that is supposed to improve his confidence. Instead of improving his confidence, he turns into Captain Chipmunk who has various wooing abilities such as singing and being charming. After two nights, he figures out that he himself is Captain Chipmunk. Alvin then cooks up a plan to get Brittany back from "Captain Chipmunk."
- "Captain Chipmunk"
- "I Give Up On You"
- "Tell Him" originally performed by The Exciters.
- This marks the first time where Simon wears blue glasses, with "clear" lenses, and when Jeanette wears pink glasses.
- This is one of the few instances where Jeanette is seen without her glasses.
- First appearance of The Chipettes' Treehouse.
- This was the first of two specials based on the Ruby-Spears cartoon series, showing up in syndication as a regular episode.
- The last Bagdasarian in-credit logo.
- Part of the A Chipmunk Valentine and The Valentines Collection DVDs.