It’s a tale for the ages: boy gets girl, boy loses girl, boy creates elaborate self-referential documentary project in an attempt to win back girl’s affections.

Chicago videomaker Jack Lawrence Mayer (whose work we recently discovered through an episode of his Living Room Songs series featuring the ever-endearing Angel Olsen) followed this formula, and the result is the 16-minute short, How To Say I Love You With Video. When asked to describe the project, Jack told us, “The short film is a fictional, comedic documentary of a bumbling filmmaker named Jack Lawrence Mayer who tries to make the perfect video to win back his ex-girlfriend.”

Opening with a live performance of local three-piece Midnight Moxie performing a hesitant cover of Townes Van Zandt‘s No Place to Fall, the film explores elements of Jack’s psyche following the dissolution of his relationship, including a montage of the things she left behind and a reality check from a friend, who describes it as, ”some self-absorbed jack’s video diary.”

We spoke with Jack about the project, its influences and consequences in an interview you can read on the next page (we suggest watching the video before clicking through!).