In the Mood for Heartbreak: 5 Angsty Movies to Watch on Valentine's Day!

Valentine’s Day can often feel like a needless holiday, especially if you’re not one of the lucky few in a relationship. But the day isn’t only about celebrating romantic partnerships; it’s about love in all its forms, including its messier, more painful ones. Heartbreak can be just as cathartic as falling in love. It’s visceral, all-consuming, and deeply human. If you agree, we’ve compiled a list of 5 unconventional films to watch this Valentine’s Day to get deep into your feels. 

1. Past Lives (2023) 

Two childhood sweethearts, Nora (Greta Lee) and Hae Sung (Teo Yoo), are separated when Nora’s family emigrates to the United States, only to reunite years later, first virtually in their early-20s and then in person as adults, when Nora is married. At times, you can’t help but hope she will leave her husband, but that desire is beside the point. This is not a story about choosing one love over another. Instead, it suggests that love can take many forms and exists across time and space. A relationship does not have to last forever to be meaningful. Some loves are bound to a particular moment in life, and their intensity is not diminished by their loss. (Stream on HBO Max)

2. The Worst Person in the World (2021) 

This Norwegian romantic comedy-drama captivated audiences worldwide upon its release. A modern coming-of-age story, the film follows Julie (Renate Reinsve), a deeply human and imperfect woman in her late-20s, as she navigates her career and love life. The film resists a neatly-tied ending, instead mirroring real life where relationships shape who we become without necessarily defining us. (Stream on Tubi)

3. Before Sunrise (1995)

A modern classic, Before Sunrise follows Jesse (Ethan Hawke), an American traveler, and Céline (Julie Deply), a Parisian student, who meet on a train and impulsively decide to spend the day together in Vienna. Over the course of the day, they wander the city, discussing philosophy, love, and their fears for the future, while revealing very little about the lives they will soon return to. The anonymity in their intimacy makes it both fleeting and profound, cementing the film as one of modern cinema’s great love stories. (Available on VOD/Digital)

4. Brokeback Mountain (2005) 

Set against sweeping American Western landscapes, this devastating love story follows two cowboys (Jake Gyllenhaal and Heath Ledger) in the 1970s whose relationship is constrained by homophobia. With its aching performances and beautiful cinematography, the film captures a love shaped by silent longing. It’s a heartbreaking reminder that some of the deepest loves are the ones never fully lived. (Available on VOD/Digital)

5. Journey to Italy (1954)

Part of Ingrid Bergman’s iconic collaboration with her then-husband, director Roberto Rossellini, Journey to Italy follows a British couple (Bergman and George Sanders) whose marriage is quietly unraveling as they travel through Italy after inheriting a house. As they move through Italian ruins and landscapes, their relationship is tested and transformed. The film culminates in one of cinema’s most sublime and unforgettable final scenes. (Stream on HBO Max and Tubi)

Happy(?) Valentine's Day!