Director Adrian Lyne and Demi Moore often fought on-set over her character, with Woody Harrelson trying to be mediator between the two. Lyne had argued that he wanted Moore to show vulnerability, while the actress defended herself. It was later while Lyne was editing this movie that he realized she was portraying what he wanted all along, and he soon apologized to Moore.
Director Adrian Lyne was originally dismissive of casting Woody Harrelson as David, but changed his mind after watching Homens Brancos Não Sabem Enterrar (1992). Harrelson said in one interview that doing love scenes with Demi Moore was uncomfortable because he was good friends with Moore's then-husband, Bruce Willis.
The tears shed by Demi Moore in the touching "girl that got away" scene in which Gage describes a past chance meeting with a beautiful girl are genuine. This scene was filmed without co-star Moore knowing any of Redfords dialogue, instead just being told to listen.
During the auction scene, John Gage (Robert Redford) is to leave the room. Redford kept missing his cue because he was listening to the jokes that auction emcee Sir Billy Connolly was saying.
Originally designed as a starring vehicle for Tom Cruise and Nicole Kidman, with Warren Beatty taking the part of the billionaire.