- Author's Saving Throw: Literally the entire reason this movie exists is that John Hughes was upset at the Executive Meddling that changed the ending of Pretty in Pink, so he wrote a very similar story while only changing the genders so it wouldn't be quite so obvious.
- Dawson Casting: Stoltz and Thompson played teenagers at the age of 26 (Masterson was 20 while Sheffer was 27).
- The Other Marty: When Martha Coolidge was hired to direct, she cast Kim Delaney as Amanda Jones and Kyle MacLachlan as Hardy Jenns. When Coolidge dropped out before filming was to begin, and Howard Deutch replaced her, he replaced Delaney with Lea Thompson (after Eric Stoltz suggested her for the role) and replaced MacLachlan with Craig Sheffer.
- Romance on the Set: Howard Deutch and Lea Thompson fell in love while filming this film, and they are now married.
- Throw It In!: Elias Koteas improvised much of his lines and actions. When Duncan puts his head on Amanda's shoulder, Lea Thompson's surprised laugh was real.
- What Could Have Been:
- The original script for this movie was actually a lot funnier than the one they filmed. Director Howard Deutch was having trouble casting for the original script, and was sacked. John Hughes then rewrote the script to be more dramatic, and eventually Deutch was rehired as the director.
- Part of the reason the original, more comedic script wasn't filmed was that Michael J. Fox turned it down. Amusingly, the part then went to Eric Stoltz, who was originally cast as Marty in Back to the Future before being replaced by Michael J. Fox.note
- The part of Amanda was originally intended for Molly Ringwald, in what would have marked the fourth collaboration between her and Hughes. However, Ringwald declined to avoid being typecast and was looking for more adult roles. Hughes was so upset over the rejection that he never again worked with Ringwald for the rest of his life.
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