There are two ways to look at Tadpole; one as a whimsical story about a precocious boy with a serious crush on his stepmother, and the other as a serious examination of this same relationship. Tadpole belongs squarely in the former category. Looking at this film in any sort of serious manner will cause one not to enjoy it. Tadpole is the childhood nickname of Oscar Grubman (Aaron Stanford, Hollywood Ending), wise beyond his fifteen years. Other guys his age prefer listening to what's popular on the radio or checking out the cute girls in school. Oscar spends his time lost in Voltaire or thinking of ways to break the news to his stepmother Eve (Sigourney Weaver, Heartbreakers, Company Man) that he is madly in love with her.
Oscar decides that Thanksgiving break will be the right time. Eve's best friend Diane (Bebe Neuwirth, Liberty Heights, Summer of Sam) complicates matters by sleeping with him. She found him wandering the streets of New York, drunk, and took him home. It is this event that drives to the heart of Tadpole. Screenwriters Heather McGowan, Niels Mueller and Gary Winick use Oscar's paranoia at having Eve discover this event to propel Tadpole forward. Oscar's father Stanley (John Ritter, Panic, Terror Tract) notices that Oscar is acting strange, and Oscar lies by saying there is a girl at school who caught his interest. The rest of Tadpole becomes almost like a farce.
Director Winick (Sam the Man, The Tic Code) filmed using a digital camera, and the result really makes no difference. It doesn't add or detract from the story at all, aside from giving Tadpole a "raw" look. Filming took place quickly over the course of two weeks, but the film does not feel rushed. What one does get a sense of is Oscar's incredible penchant for making things more difficult than they need be. For somebody so smart, he is sure acting dumb. A lot of it comes from Diane. Oscar asks Diane not to tell anybody, and she agrees, although he never believes her. Oscar believes that if Diane tells Eve, his chances with her will disappear.
Winick never truly evokes why so many women find Oscar so irresistible. He states through his characters that single, older women love his passion, but Oscar appears more pretentious than passionate. His childishness comes out in the third act, when he truly goes nuts. Any attempts to make any sort of statement on relationships of this ilk disappear in childish and amusing scenarios. Throughout the movie, Stanford and Neuwirth give amusing performances. Neuwirth in particular plays a devilishly sly and smug older woman, who is having fun toying with such a young boy.