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  • Actor-Inspired Element: Nora Ephron credited Meg Ryan not only with the idea of faking an orgasm in the famous restaurant scene, but also with the idea of setting it in a restaurant in the first place.
  • California Doubling: They drive off the University of Chicago campus on the south side to New York.... via a picturesque segment of Lake Shore Drive headed toward the south side [Did they have to visit a friend at Northwestern, Depaul or Loyola first?]
  • Colbert Bump: Katz's Deli, the site of the Fake Orgasm scene, was cemented as a New York landmark because of it. Now there's even a sign pointing out the very table.
  • Creator Recovery: Rob Reiner got the idea for the film after his divorce from first wife Penny Marshall, and the string of complicated relationships that had preceded this marriage. He was going to have Harry and Sally not end up together, to reflect his view of relationships at the time. However, he met his subsequent (and current) wife while developing the film, and their marriage inspired him to change the ending so Harry and Sally do get together after all.
  • The Danza: Carrie Fisher plays Marie Fisher.
  • Extremely Lengthy Creation: Nora Ephron wrote the screenplay, and its numerous drafts, over a period of nearly five years.
  • Method Acting: To help him capture the mood of a newly divorced, single man, Billy Crystal would hole himself up in a hotel room in isolation, deliberately keeping himself away from cast and crew.
  • Real-Life Relative: Rob Reiner's mother delivered the famous line, "I'll have what she's having".
    • Reiner's daughter Tracy plays one of Harry's girlfriends.
  • Romance on the Set: Rob Reiner met his second (and current) wife, photographer Michelle Singer, while making this movie. This even inspired him to give the film a happy ending.
  • Star-Making Role: For Meg Ryan as a leading lady.
  • Technology Marches On: The Casablanca scene. If the movie was made today, Harry and Sally most likely would have watched the movie over a Discord or Skype call, rather than flipping to the same channel and calling each other.
  • Throw It In!:
    • The famous "I'll have what she's having" line was suggested by Billy Crystal.
    • Harry's weird accent in the museum. Meg Ryan's reaction is real; you can see her glance off-screen at Rob Reiner.
    • The "Win, Lose or Draw" scene was entirely improvised.
    • Harry and Sally's final interview at the end of the film was completely improvised.
  • Underage Casting: Meg Ryan was 26 years old playing a woman whose age ranges from 21 to 33, and whose ticking biological clock is an important theme in her character development. By contrast, Billy Crystal was 40 years old, playing a man whose age ranges from 25 to 37.
  • What Could Have Been:
  • Working Title: Nora Ephron originally wanted to call the film How They Met. Other options were Just Friends, Playing Melancholy Baby, Boy Meets Girl, Blue Moon, Words of Love, It Had To Be You, Harry, This Is Sally and Scenes From A Friendship.
  • Write What You Know: The film was based on Rob Reiner's experiences post-divorce and as a single man. Ironically, Reiner met his current wife during the making of this film.
  • Write Who You Know: Harry and Sally are based on Rob Reiner and Nora Ephron. Many of their interactions are based off of Real Life conversations between friends Reiner and Crystal.

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