How to Make the Cruelest Month premiered at the 1998 Sundance Film Festival, where it was nominated for the Grand Jury Prize. It won the Best of Fest prize at the 1998 Long Island Film Festival.
Writing for Variety, Emanuel Levy gave the film a mixed review. He praised the director's ideas and characters, as well as his sensitivity to the issues faced by young Americans. He drew comparisons between the film and Woody Allen's early films ("in spirit and ambition, if not in execution"). He enjoyed DuVall's performance, although said it was "occasionally too intensely mannered", and praised the rest of the cast. However, Levy also described the film as uneven, with a "messy structure and lack of discipline".