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Film: Pretty In Pink

A 1986 film starring Molly Ringwald as Andie Walsh, a teenager with a crush on an upper-class boy, Blane McDonough (Andrew McCarthy). When he turns out to reciprocate her feelings and they pursue a relationship, their respecive social circles show some resistance.

Andie lives on the Wrong Side of the Tracks with her unemployed, divorced father (played by Harry Dean Stanton), who she cares for, almost like a mother. Her best friend Duckie (Jon Cryer) is in love with her, but plays it off as a joke to maintain their friendship. The two of them are harrassed by the "richie" kids, Steff (James Spader), and Benny (Kate Vernon). Andie works for her older friend Iona (Annie Potts) at TRAX, a New Wave music store in Chinatown. Iona urges her to go to the prom. One of the Brat Pack movies. Written (but not directed) by John Hughes.

This film provides examples of:

Cleaning Up Romantic Loose Ends: One of the more egregious examples.
Dogged Nice Guy: Ducky, to Andie.
Hey, It's That Guy!: "And yes, that is the guy from Two and a Half Men." - Lorelai Gilmore.
Precision F-Strike: When Blaine cancels his prom date with Andie, saying that he already asked someone else and forgot about it, she calls him a "filthy, fucking, no-good liar". This is the only time the word is used in the film.