Kevin Smith wrote the script inspired by his experience with then-girlfriend Joey Lauren Adams, who plays Alyssa.
This film was reportedly just two votes away from an Academy Award nomination for Best Original Screenplay, according to Kevin Smith's podcast.
Joey Lauren Adams wrote the song she sings. It was originally a country song, but Kevin Smith requested they pump it up a bit.
When Kevin Smith pitched the idea to Miramax, he also said that he had written the parts with his friends Ben Affleck, Jason Lee, and Joey Lauren Adams in mind. Miramax, however, wanted to cast people who already had celebrity status, such as Jon Stewart, David Schwimmer, and Drew Barrymore (these three were actually suggested). The film's original budget of $3 million depended on Miramax's support. Ultimately, Smith suggested that he make the movie with his three original actors on his own, and Miramax could buy it for distribution if they liked it. Miramax owners Bob Weinstein and Harvey Weinstein liked this idea, and gave him $250,000 to make the movie (1/24 of the budget of his previous film, Mallrats (1995)).
(at around 13 mins) During the scene where Holden and Alyssa are playing darts, men are going in and out of the women's bathroom and women are going in and out of the men's bathroom.
Kevin Smith: [off-screen grab] (at around 32 mins) When Banky asks whether Alyssa looks at herself in the mirror, Holden grabs him and pulls him from off-camera.
Kevin Smith: [Star Wars] (at around 6 mins) Hooper (Dwight Ewell) gives an inflammatory speech about this series of films.
Kevin Smith: [hockey] Holden and Alyssa break up at a hockey game. Alyssa is wearing a Toronto Maple Leafs jersey. Holden and Banky are also playing hockey on Sega Genesis, which Jason Lee's character Brodie does often in Mallrats (1995).