Quote:
Based on the approximate age Luke was supposed to be, Pretty in Pink would have been a popular movie when he was a teenager. If he did any dating at all, odds are he saw it and other John Hughes movies like The Breakfast Club, Weird Science, Sixteen Candles, Ferris Bueller's Day Off, and Some Kind of Wonderful.
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I can totally picture Luke at the theater with a girl, watching a movie he hates, but since he likes this girl (Rachel? assuming they dated long before they really got together) he is willing to watch it.