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).
Wanting to depict the fictional town as being like any other working class town in America, Ted Demme drew inspiration from The Deer Hunter (1978) and had the film screened for the cast and crew. Demme cited the first third of that film as depicting real friendship.
Paul's monologue to Will, "A beautiful girl can make you dizzy, like you've been drinking Jack and Coke all morning. She can make you feel high full of the single greatest commodity known to man - promise. Promise of a better day. Promise of a greater hope. Promise of a new tomorrow. This particular aura can be found in the gait of a beautiful girl. In her smile, in her soul, the way she makes every rotten little thing about life seem like it's going to be okay." is in the intro to the demo version of a Taking Back Sunday song called, "Great Romances of the Twentieth Century".
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.
Matt Dillon's character stays home during the reunion to watch Rich Man, Poor Man (1976) and he mentions how there was never a scarier villain than 'Falconetti,' played by William Smith. Dillon had appeared in two movies with William Smith, The Outsiders (1983) and Rumble Fish (1983). In both movies, he played the antagonist to Smith's character.