In 1999, Thiago Da Costa collaborated with filmmaker Ben Nedivi while the two attended NYU Film School, and together they created THE LOVE SONG OF HENRY MILK. With an original script and strong direction by Ben, the film tells the story of a lonely cybernerd's descent into semi-madness when his computer breaks down and he is forced to attempt human interaction unmediated by the machine.

The film warned about the potential negative aspects of the internet insofar as its potential for isolating people instead of bringing them together. It hit a nerve and it ended up gathering accolades from all that watched. At NYU's First Run Film Festival, it became a finalist for the prestigious Wasserman Award. Later on, the film was picked up by Hypnotic for distribution and was shown multiple times on the Sundance Channel and on Japanese television.