Simpleton Grace wears a leather mask and lives in a trunk. He is awoken one day to learn of his mother’s passing. Reeling from the news, he must return to his childhood home to confront the many failed relationships of his past. One relationship of note was with childhood sweetheart Daisy who ended their relationship when Simpleton gave her a rather unconventional Valentine’s Day gift. The Simp Takes a Holiday asks the question, can there be redemption for even the most strange among us?