This John Huges film (The Breakfast Club, Ferris Beuler's Day Off) is about a high school senior girl (played by Molly Ringwald [The Breakfast Club, 16 Candles]) and her social/romantic interactions in an environment that has a strong divide between the wealthy and not-so-wealthy. She's one of the have-nots. Her best friend (your quintessential "friendzoned" guy) is played by Jon Cryer (Two And A Half Men. James Spader (Wolf, Stargate) plays a douchebag rich kid who resents Ringwald for spurning his advances, and Andrew McCarthy (St. Elmo's Fire, Weekend At Bernie's) plays his best friend who is miraculously a nice rich guy and has mutual interest in Ringwald.Annie Potts (Designing Women) is her slightly older best female friend who works at the record store. They keep saying how she's older, but I just thought she was adorable. She just has one of those young sweet faces, and her higher pitched voice (thankfully not Fran Dresher-like) and bubbly personality make her seem young too. Though she was clearly beyond high school years. Actually, it was weird seeing much of the cast so young, James Spader and Jon Cryer particularly. Harry Dean Stanton played the single father of Molly Ringwald and I found him to be extremely likable. His face naturally has a drooping scruffy look to it, but you could feel the warmth and his love for his daughter through the screen. He's underemployed (working part time, not unemployed) and depressed at the loss of his wife and mother of his child (she packed up and left, not died) and many other movies would make him an angry person or an alcoholic or too lazy to work at all, but he was actually trying and has a great relationship with his child and I liked that.
The story had various events in it, but not much in the way of character arcs. The main character dates a guy because he is attractive despite him being the other (monied), and she doesn't really change much. Spader's character provides the main conflict of the film, but his character isn't really developed beyond the bassic MacGuffin. Some of the side characters have an arc and grow, but it's almost completely off-camera and we just suddenly see them in their grown iteration later on (particularly Potts' character). The one strong development is in the father character. If you're a big fan of Molly Ringwald, this is pretty much her quintessential film, so you should watch it. If you've ever been in the friendzone and hated it, then avoid this film like the plague: it'll drive you into a homicidal rage. This film is definitely of a time and pretty much will feed a craving for '80's nostalgia, and that's its main draw. I prefer The Breakfast Club, possibly because it was the first of the Brat Pack films I'd ever seen, but it was all about character development and had a broad cast of fleshed-out characters. Though I saw it far later, I also prefer St. Elmo's Fire for the development, despite not liking all of the characters personally. Also Pretty In Pink is definitely from a female perspective so I can't connect with it as effectively. Definitely more recommended to a high school or middle school girl than for a male of other ages. I don't remember my high school experience including such antagonism between the wealthy and middle class, but maybe I just came from a more homogenous town; also, the '80's were a time of booming economy and a lot of suddenly-rich people establishing a strong subculture (watch American Psycho for a thorough analysis). For me the movie is only about 2.5 stars, though I can see how it could resonate with someone if they're at a certain point in their life or if they have a strong nostalgia for it. But keep that in mind if you're considering watching it for the first time.
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