With Valentine’s Day just around the corner, this is the perfect time to plan your watch lineup for the occasion. If you’re tired of the usual feel-good love stories and crave tragedy and drama, then this is the list for you!
Here are our favorite movies and series that offer a more complex — and often uncomfortable — take on love and romance. Binge-watch these flicks at your own peril!
Tom (Joseph Gordon-Levitt), a greeting-card writer and hopeless romantic, is blindsided when his girlfriend, Summer (Zooey Deschanel), unexpectedly breaks up with him. He looks back on their 500 days together, trying to understand what went wrong in their relationship.
Spoiler alert: It doesn’t follow the typical romantic comedy formula where everything works out in the end. Instead, the film shows that not all relationships are meant to be and it focuses on personal growth and acceptance after heartbreak.
This film is a drama-comedy that explores the search for love and purpose in modern Oslo. It follows four years in the life of Julie (Renate Reinsve), a young woman who grapples with the complexities of her love life and the uncertainty of her career, ultimately prompting her to confront her true self.
It offers a more realistic and introspective approach to exploring themes of love, identity, and personal growth. The film doesn’t have a neat, idealized solution. Instead, it shows the messy, unglamorous sides of exploring relationships and self-discovery.
Clementine (Kate Winslet) undergoes a procedure to erase all memories of her ex-boyfriend, Joel (Jim Carrey) after their breakup. When Joel finds out that Clementine is taking drastic measures to forget their relationship, he decides to undergo the same procedure and starts to lose the memories of the woman he once loved.
Blending elements of sci-fi and relationship intricacies, this film doesn’t romanticize relationships. It depicts them as complicated, messy, and sometimes painful, offering a more realistic and raw portrayal of human connection.
Nora (Greta Lee) and Hae Sung (Teo Yoo) are childhood friends with a deep bond, but become estranged when Nora's family moves from South Korea. Two decades later, they are reunited in New York for a week, where they explore ideas of destiny (“in-yun”), love, and the decisions that shape life.
The film delves into how destiny can be fundamentally changed by life experiences, and how that affects people’s ability to reconnect. It asks the question “what could have been,” as it explores how life paths and choices can change the course of relationships.
The story follows Marianne (Daisy Edgar-Jones) and Connell (Paul Mescal) who come from different backgrounds, yet share the same small town in Ireland. They continuously cross paths in each other’s romantic lives.
The series showcases the nuance of relationships in a realistic way — focusing on the quiet, sometimes painful moments of intimacy, vulnerability, and miscommunication. It presents the raw portrayal and often relatable aspect of love; messy and uncertain.
This limited series follows Emma (Ambika Mod) and Dexter (Leo Woodall) parting ways after graduation, but fate has other plans, bringing them together unexpectedly.
It emphasizes the idea that love isn’t about a perfect match or a smooth path. It also shows that relationships evolve, people grow apart and come back together, and life can sometimes take you in unexpected directions.
Our Millennial editor insisted we mention that the 2009 David Nicholls novel this series is based on was also adapted into a maudlin 2011 film starring Anne Hathaway. You can watch both and let us know which version tugs at your heartstrings more.
The main plot of Fleabag’s (2016) second season revolves around the main character’s (Phoebe Waller-Bridge) complicated relationship with a Catholic priest (Andrew Scott). As she navigates her feelings for the priest, she continues to face strained familial relationships, from her distant father to her complicated bond with her sister.
The series combines dark humor and emotional vulnerability in a way that feels personal and relatable. Their chemistry is built on emotional depth rather than conventional romance as both characters grapple with their own issues and desires.
(In case you’re wondering where the famous “It’ll pass” line came from, it’s from this show!)