Young Timmy starts as a window cleaner in the little company of his brother. Soon he learns that some female customers expect additional service. Young and curious as he is, he reluctantly accepts the juicy duty. However his heart belongs to Liz, who demands the highest commitment until she lets him go all the way.

Henry Roth (Sandler) is a veterinarian living in Hawaii who enjoys the company of vacationing women. He leaves the playboy life behind after he falls for Lucy (Barrymore), who suffers from short-term memory loss. Since she can never remember meeting him, Henry has to romance Lucy every single day and hope that she falls for him.