In which 2017 short film does a man named Frank find himself in a series of unfortunate events on the titular romantic holiday, leading him to question its meaning?

While the title F Valentine's Day (Review) is indeed the correct answer, the film described in the trivia question has a few key differences from the actual movie. The film in question, often stylized as "F*ck Valentine's Day," was released in 2025, not 2017, and it features a protagonist named Gina, not Frank. Gina, who was born on Valentine's Day and resents the holiday, finds herself in a series of chaotic events during a trip to Greece, where she attempts to prevent her boyfriend's impending proposal. This leads her to critically examine her relationship and the true meaning of love and commitment.

Directed by Mark Gantt and starring Virginia Gardner as Gina, alongside Marisa Tomei and Skylar Astin, the film offers a comedic and often introspective look at the pressures and expectations surrounding Valentine's Day. Gina's journey of self-discovery, fueled by her disdain for the romantic holiday, explores themes of personal growth, the timing of relationships, and challenging societal norms around love. Despite the discrepancies in the trivia question's details, the core idea of a character facing unfortunate circumstances on Valentine's Day and questioning its significance remains central to the film's narrative.

The movie blends humor with honest reflections on relationships and individual choices, suggesting that love isn't always convenient or smooth. Gina's initial attempts to derail a proposal on her least favorite day ultimately lead her to a deeper understanding of herself and what she truly desires in a partner. This makes "F Valentine's Day" a fitting, albeit slightly different, answer to the spirit of the trivia question, highlighting a character's challenging experience with the titular romantic holiday.