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How I Got Into College (1989)
From Amazon:
This diverting (if very unrealistic) comedy focuses on the exploits of charmingly naive Marlon Browne (Corey Parker), a well-meaning but scholastically average high school student intent upon attending the same college as the girl of his dreams, his classmate Jessica Kailo (a young, perky Lara Flynn Boyle). To Marlon, Jessica seemingly has it all: looks, intelligence, and sophistication. His dilemma is that she is a far brighter student whose main choice, Ramsey College, seems hopelessly out of his reach, so the awkward but determined Marlon endeavors to get accepted there. But little does Marlon know that Jessica is also struggling with...
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