I remember they were in college and the one frat guy had this smarter guy write love letters and help him get this girl he liked, not only that but he also help with the way he talked to women all to get this one girl, but the guy writing the letters also liked her. The frat guy hired a hooked for the writer at one point so that they could go on a double date. They go to a fancy type restaurant and the hooked orders fruit loops and beer. The frat guy ends up leaving the school in the end and the chick figured out who actually wrote the letters and confronts him holding the entire stack of letters which all start blowing away.
“Wimps” (1986)?
http://www.imdb.com/title/tt0092217/
OMG Thank You so much been searching for 5 Days for this movie title
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