In the fight scene, Robert cries a little bit and turns his back to the camera, so we don't see him. When shooting the scene, Meryl Streep asked Clint Eastwood why he was filming it like that, if by doing so he was missing the opportunity to shine as an actor. Eastwood replied that the scene worked better without seeing Robert cry directly. Streep was then amazed and have praised the director's talent for thinking more about the moment than his chance to shine as an actor.
One of the few PG-13 rated movies to use the word "fuck" in a sexual context (Francesca's line "...or should we just fuck on the linoleum one last time?"). The MPAA originally rated it R solely because of this line, but Clint Eastwood successfully appealed them to re-rate it.
The studio was initially only interested in casting younger actresses in the lead but were failing to find anyone suitable. The idea to talk to Meryl Streep largely came from Clint Eastwood's own mother, Ruth Wood.
Robert James Waller finished his manuscript in eleven days, intending it to be simply a gift for various friends and family. One of his friends was so impressed with the manuscript, he asked if he could try to interest a literary agent in the work. Waller later received a life-changing call from a New York agent who asked, "...Robert, where have you been all my life?"
Even though she wasn't a part of those scenes, Meryl Streep went to the set to meet Annie Corley and Victor Slezak, who played her kids when they are adults. They both said that the meeting helped them to portray the memory of Francesca as a character better.
Clint Eastwood's then live-in girlfriend Frances Fisher proposed herself to play the adult version of Francesca's daughter. That was rejected by Clint. Fisher had hoped to play "any part" in the film because she revered Meryl Streep and simply wanted to be part of any film that starred the foremost actress of her generation; she wanted to observe Streep at work. Eastwood knew this, so he kept saying, "Next week . . ." whenever Fisher asked to visit the Iowa set. Finally, when Fisher arrived in Iowa, she discovered Streep had already gone. "Oh," Eastwood informed her, "she's done with her scenes."
Prior to this film Winterset Iowa was primarily known as the birthplace of John Wayne. This film ultimately drew a huge number of fans to the various bridges and other locations and it is still visited by Wayne fans today.