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If you haven't seen this film yet you likely won't so I offer no spoiler alert as it is 27 years old now!
Set in lovely Tuscon, Arizona where Ronald "Ronnie" also "Donald" Miller is the quite, weedy but still cute astronomy geek who has the stereotypical red-haired bestie (Kenneth played by Courtney Gains) who is also a nerd. In fact, Ronald is such a nerd that despite being a senior in high school he has never seen a "titty" which he gets plenty of opportunity to do once he becomes cool. And to make matters worse, his little brother (a very young Seth Green) is in seventh grade and cooler than he is.
Ronald has saved up money all summer, though really given the length of a summer and the rate of grass growing even with the required sprinkler systems in the Arizona desert, I cannot see how the economics of this work, by mowing lawns on what has to be his dad's riding lawn mower. Ronald now has....$1000! I know, amazing. Instead of buying himself a telescope so he can look at the moon he buys himself a pretend girlfriend.
It was okay to pimp yourself out socially for money in 1980s teen films, so long as you didn't do anything sexual. Cindy Mancini (Amanda Peterson) is the prettiest girl in school, captain of the cheerleaders and Ronald's (Patrick Dempsey) heart's desire.
There are some gems in this movie; like the scene where Ronald tells Cindy that in the future people will live on the moon. By the time he's in his 40s and his dad's age. So, you know, about now. How's that moon living going for you guys out there? Nothing like strolling by the Sea of Tranquility on your day off is there?
Or the exceptionally brilliant scene where Ronald, no longer cool, hip Ronnie, stands up to a guy who was his friend just weeks before and threatens to break the mean jock's arm for daring to rough up Kenneth. And gives a moving speech containing the line: "Nerds, jocks. My side, your side. It's all bullshit. Its hard enough just trying to be yourself." Afterwards the rest of the cafeteria (it's outdoors but they call it that in the film) all clap. It's almost enough to bring a tear to your eye.
Or the moving romantic moment where one of Cindy's best friends makes Ronald a real man:
[Patty seducing Ronald in the car]
Patty: Are you into long distance relationships?
Ronald: No.
Patty: Now, then why don't you reach out and touch someone?
[puts his hands on her bared, but not seen by the audience, breasts]
In the end Ronald realises being true to himself is being...himself and Cindy realises her friends are tools but then they're not tools because they clap and realise that it's better to all just get along. And she gives him his money back somehow - without a job or any real prospects of getting one since she seems to live off her mother's charge cards - just moments before they ride off into the sunset together on that lawn mower.
So what does this classic 1980s teen rom-com teach us? That it's okay to pimp yourself out so long as it is just hanging out. It's also okay to charge your way through life with plastic. Sex with cool kids makes you cooler except for when they're no longer cool kids and it makes you feel ashamed. Redheads are NEVER the romantic lead but always the nerdy best friend who's house gets dog shit thrown at it on Halloween and Seth Green really didn't get a whole lot taller than he was in 1987.