- Actor-Inspired Element: The scene where Gib teaches Alison to shotgun a beer was added to the script after John Cusack told Rob Reiner it was something he knew how to do.
- California Doubling: Most of the East Coast college scenes (the ones without snow) were filmed at University of the Pacific.
- Cast the Runner-Up: Anthony Edwards originally auditioned for the role of Gib Gibson before eventually playing the role of Lance. Tim Robbins also auditioned for the lead before being cast as Gary Cooper.
- Star-Making Role: For John Cusack.
- What Could Have Been: Meg Ryan was considered for Alison Bradbury.
Trivia / The Sure Thing