Henry Roth (Sandler), the local marina veterinarian, only dates tourists because he's afraid of commitment - that is, until he meets Lucy (Barrymore). Unfortunately, Lucy lost her short-term memory months ago in a car accident, and for her, each day is October the 13th. She follows the same routine every day - breakfast at the same restaurant, pineapple-picking with her dad, and eventually bed time, where sleep wipes away her short-term memory. Henry, however, refuses to be forgotten, and as his puppy love matures, he embarks on a quest to restore her memory, or at least be a part of her everyday routine. But vying for Lucy's attention isn't always easy. Henry explores various approaches before making a video for Lucy to watch every morning, reminding her of who she is and what she's doing...