Edward Burns gave Robert Redford a tape of this film in a NYC elevator and begged him to watch it. Redford said that Burns looked like a panhandler. "I get that all the time, but I thought, what the hell, that's what it's all about." He watched it, liked it, and the film went on to win at Sundance.
Seamus Egan, who composed much of the music on the soundtrack, was on a tour of New England when his car broke down. He was put up for the night by a local couple he had never met, whose adult son happened to be visiting for the weekend. They loaned Seamus their own car so he could finish the tour. In gratitude, Seamus (and bluegrass musician Dirk Powell) gave them copies of their CDs, they only gift they could afford at the time. The son turned out to be Andy Yarme, a technician working on the film in New York. The CDs found their way to Ed Burns, who in turn called Seamus and asked if he could use some of the music on the film. After the film was picked up by Sundance, the music was remastered, and due to the increased budget, Sarah McLachlan was brought on board. Together, they re-wrote Seamus' instrumental "Weep Not For the Memories", creating the hit "I Will Remember You". McLachlan's video for the song following its release as a single cost three times to make as the entire Brothers McMullen production.
Maxine Bahns was Edward Burns's girlfriend at the time the film was being made. As a favor to her boyfriend, Bahns agreed to help him with the auditions by reading opposite the various actors trying out for roles. Eventually Burns asked her to take the part, although it meant that Bahns had to forego a trip to Paris to study at the Sorbonne.
Filmed every weekend over an eight-month period. For the scene where Edward Burns's character goes on a date in Central Park, the first part was shot in October, the second in January and the last part in April.