Producer/Writer/Director Anthony Kilburn reportedly completed the first draft of the script in only seven days.
Co-Director Anthony Brooks was originally interviewed to film a behind-the-scenes documentary about the making of Chiaroscuro, Baby (2009), but when he became enthusiastic about the script, he was hired on as Assistant Director instead. His contributions to the film became so great, his title was eventually changed to Co-Director.
While principal photography lasted two months, filming only took place on a total of 33 days, most of which were limited to five-hour-long shoots on weekday evenings.
The sound department had constant problems during shooting. To emulate the sound quality of 1960s films, an analog cassette recorder was used, with digital recording as a backup. The analog recorder would often pick up faint radio signals on tape, rendering audio worthless. Also, the digital mixer employed on set frequently failed, forcing the audio department to rely on post-production editing to accomplish the desired sound design.
When a local club backed out of a shoot last minute, filmmakers were forced to compromise on a bar across town. When they arrived at the new location, they discovered the bar was not only open, but that the club next door had live music which could be heard through the walls. Director Anthony Kilburn decided to continue with the shoot but planned on recording the audio with Automated Dialog Replacement. By the time filming commenced, the bar's patrons remained quiet for each of the four takes required to capture the scene, and during the best take, there happened to be a pause in the live music next door; No ADR was necessary. The scene is the one in which Calvin and Alice first meet.