Can’t Buy Me Love (1987)

I cut grass from 15 to 25 years old and that’s how I put myself through college and even made extra money once I started my advertising career. I certainly would not have used the money I made to save for a telescope or to date the popular girl in school like Ronald Miller (Patrick Dempsey).

The girl next door of his dreams, cheerleader Cindy Mancini (Amanda Peterson, whose career and life didn’t go as brightly as this movie would seem to make me think that it would), has wrecked her mother’s new suede dress, so she agrees to be his girlfriend for a month for the sum of $1,000.

This is the kind of movie that makes me hate the second act of the three-act structure. Ronald gets popular, gets rid of his old friends and even turns on Cindy. She thought they were in love and he probably did as well, but no one knows how to connect. He’s already hanging out with her friends instead of Malachi and Seth Green, but isn’t that the way these things always go.

Director Steve Rash started his career making movies like The Buddy Holly Story and Under the Rainbow and now makes direct-to-video sequels to the American Pie, Road Trip and Bring It On films.

So yeah. In the 80s, a tender romantic comedy about making young women into prostitutes was the kind of thing we saw as romance. Weird, huh?