One reasonable way to judge a romantic comedy is to ask how strong a rooting interest the viewer has in the coupling that is destined to occur at the end of the film. In Win a Date with Tad Hamilton!, the desire is lukewarm. The central flaw here isn't the predictability of the plot (that's a given in any film of this genre) or the absence of crisp dialogue, but the lack of conviction with which two of the three lead characters are presented. It's tough to develop a compelling romantic triangle when two-thirds of the participants aren't being effectively "sold."
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