The movie was inspired by the experiences of screenwriter Scott Rosenberg when returning home to Needham, Massachusetts. During what he claimed was the worst winter for his hometown, he was waiting to see if his script Con Air (1997) was going to be produced and was getting fed up with writing action movies. Rosenberg cited that there was more action happening with his friends not wanting to accept that they were turning 30 or had commitment issues, which became the basis for Beautiful Girls (1996).
Ted Demme had the cast come to Minneapolis and live with each other for 2-3 weeks so they could bond.
Tony Scott turned down a chance to direct, because he felt he couldn't do justice to Scott Rosenberg's script, which placed characterization and dialogue above dramatic event.
The scene where the cast breaks into a rendition of "Sweet Caroline" in a fictitious, small-town New England gin mill predates the tradition started in 1997 by the Boston Red Sox Fenway Park faithful who have joined in the singing of the Neil Diamond classic ever since. The film's tagline, "Good times never seemed so good," is taken from that song's chorus.