Released in January of 2009, this DVD features episodes centering around Valentine's Day and romance in general.
A Chipmunk Valentine: Brittany is anxiously awaiting for Alvin to ask her to the Valentine Ball, but Alvin will have no part of it. He's suffered his share of heartbreak in the past, and can't handle another rejection. In a dream state from listening to some self-esteem tapes, he becomes Captain Chipmunk, heartbreaking ladies man.
Dr. Simon and Mr. Heart-Throb: While being interviewed by Toddler Beat, Alvin accidentally messes something up in Simon's lab. When Simon gets a hold of the mistake, he becomes the handsome and dashing Mr. Heart-Throb. Being able to woo the girls with ease, he comes to prefer his alter-ego.
Dear Diary: The Chipettes get their own diaries, but can't help snooping in each others, leading to a gross misunderstanding and fight for the heart of a boy.
Theodore and Juliet: Try as he might, Theodore can't get the girl he likes to notice him. What's worse, she likes Alvin!
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