Please Advise is a lovelorn office dramedy about Miles Dempsey, a 32-year-old marketing copywriter and musician approaching the one-year anniversary of his wife’s accidental death, for which he feels partially responsible.

Miles works at a struggling San Francisco consumer audio company, where he develops a crush on Sara, a new temporary graphic designer and fellow musician. As they collaborate on package designs and play music together after hours, their professional and creative worlds become entwined in a way that brings their personal demons into sharp relief and emphasizes their divergent romantic and career aspirations. Complicating matters are Miles's own unresolved guilt, a gallery of oddball co-workers, and Sara’s own tumultuous past.

Miles tries various coping methods to relieve his grief. He writes an advice column on a coffee shop bulletin board, pursues lucid dreaming and therapy, and gets back to work on the demos he's hoping might help woo Sara and change his life. When Miles's boss also takes an interest in Sara, things come to a head at an industry trade show in Vegas. Having already been a victim of fate, and determined not to lose what could possibly be the next great love of his life, Miles decides on a course of action that could win Sara—or cost him everything.