9. After turning down a role in Forrest Gump, a move he regretted after it became an instant hit, comedian Dave Chappelle, then 24, was keen to play Kevin, Joe Fox’s business partner and dating guide. Ephron gave Chappelle free rein to improvise any and all of his lines. ”I don’t think there was anyone else on the list,” script supervisor Dreyer said in I’ll Have What She’s Having. “He proved to be a delight and everything she thought he was.”
10. Sara Ramirez played the cashier in the cash-only line at Zabar’s. The scene was based on something that happened during production on Sleepless in Seattle, where a mystified Ephron watched as her first AD on that film had a similar impact on a concierge at the airport.
Oh, and it was the first and last time Zabar’s has ever let a movie film inside the iconic grocery store. And they weren’t the only New Yorkers who weren’t exactly thrilled with the massive production taking over their city.
During one shoot in a restaurant on the Upper West Side, a man started banging on the window, yelling, “Nora Ephron! Nora Ephron! I thought you loved this neighborhood? Why are you f–kin’ with us?!’ per cinematographer John Lindley. She was eventually able to calm him down.
11. Chris Messina, who would go on to play Mindy Kaling‘s love interest (and the Internet’s boyfriend, Danny Castellano) on The Mindy Project, actually had a small role in the movie. He played the clueless sales associate working at Fox Books who needs Kathleen’s expertise when it came to “The Shoe Books” series by Mary Noel Streatfield.