by Savannah Motbey
Romantic comedies have trained audiences to expect a certain formula. Two people meet, face obstacles, and end up together by the time the credits roll. The pattern repeats across decades of filmmaking, and yet some of the most compelling work in the genre comes from directors willing to abandon that script entirely. These films take on relationships that exist in grey areas, where power dynamics are uneven, where motivations are mixed, and where love itself might be beside the point.
What follows is a selection of films that treat unconventional romantic arrangements with honesty and, in some cases, sharp humour. They show relationships built on transactions, secrecy, age gaps, and social taboos. They avoid easy resolutions.
Films That Frame Relationships Outside the Expected
Cinema has long found material in romantic arrangements that fall outside ordinary dating patterns. Anora, the 2024 Sean Baker film, follows Ani, a young sex worker who marries the son of a Russian oligarch. The movie swept five Academy Awards including Best Picture and Best Director, and it shares the rare distinction of winning both the Palme d’Or and the Oscar for Best Picture. Mikey Madison took home Best Actress for her performance. Anora is currently streaming on Hulu in the US.
Shiva Baby, the 2020 Emma Seligman comedy, places its protagonist in an acutely uncomfortable family gathering. Rachel Sennott plays a directionless bisexual woman who runs into both her ex-girlfriend and her sugar baby arrangement’s married partner at a shiva. The film holds a 97% positive rating from 147 critics on Rotten Tomatoes and ranked as the most-watched title on Mubi in 2021. Netflix in the US added it in December 2024.
Why Anora Works
Sean Baker built his reputation on films about people who live at the margins of American life. Tangerine, shot entirely on iPhones, followed transgender sex workers in Los Angeles. The Florida Project looked at families living in motels near Disney World. Anora continues this pattern.
Mikey Madison plays Ani with a toughness that never tips into caricature. She knows what she wants from life and has figured out a path toward it. When she meets Ivan, played by Mark Eydelshteyn, at the strip club where she works, the two begin a relationship that moves fast. Ivan proposes marriage. The wedding happens in Las Vegas. The problem is that Ivan’s family has money and influence, and they have no intention of allowing the marriage to stand.
The film handles its subject with care. It does not sentimentalise Ani or portray her as a victim in need of rescue. Her choices are her own. The humour comes from the absurdity of her situation, caught between a feckless young man and the operatives that his family has sent to clean up the mess. The drama comes from watching someone fight for what she believes she deserves.
Shiva Baby and the Comedy of Discomfort
Emma Seligman made Shiva Baby as her thesis film at New York University before expanding it into a feature. The movie runs 77 minutes and takes place almost entirely in a single location. Danielle, played by Rachel Sennott, dreads family gatherings under normal circumstances. This one forces her to confront multiple aspects of her life that she has kept separate.
Her parents do not know about her sugar arrangement. They do not fully understand her sexuality. When she runs into Max, the older man she has been seeing for money, she learns that he has a wife and a newborn child. To make matters worse, her ex-girlfriend Kim is also at the shiva.
The film generates tension from social embarrassment. Seligman uses a score that builds anxiety, treating the cramped house like the setting of a horror movie. Danielle has nowhere to escape. She cannot explain herself to anyone. The comedy is painful to watch in the best way.
The Graduate Still Holds Up
Mike Nichols directed The Graduate in 1967, and it remains one of the most referenced films about unconventional relationships. Dustin Hoffman plays Benjamin Braddock, a recent college graduate with no plans for his future. Mrs. Robinson, played by Anne Bancroft, seduces him. She is the wife of his father’s business partner.
The affair gives Benjamin something to do. It is not love. He is bored and adrift, and she is bored and bitter. Their arrangement is transactional in its own way, even without money changing hands. When Benjamin meets her daughter Elaine, played by Katharine Ross, the situation becomes more complicated.
The ending of The Graduate has been interpreted many ways. Benjamin and Elaine sit on the back of a bus after he has interrupted her wedding. Their expressions are uncertain. The film does not promise a happy outcome. It asks what happens after the grand gesture, after the chase, after the conventional romance plot has played itself out.
Punch-Drunk Love and Isolation
Paul Thomas Anderson made Punch-Drunk Love in 2002 with Adam Sandler in the lead role. This was unexpected casting. Sandler had built his career on broad comedies, and Anderson was known for ensemble dramas like Boogie Nights and Magnolia.
Barry Egan runs a small business selling novelty toilet plungers. He has 7 sisters who berate him constantly. He struggles with anger and social anxiety. When he calls a phone sex line out of loneliness, he ends up being extorted by the company. His relationship with Lena, played by Emily Watson, develops under these strange circumstances.
The film treats Barry’s condition seriously. His violence comes from years of suppressed emotion. His connection with Lena is not cute or easy. She accepts him, and that acceptance feels earned because the movie shows how difficult he is to be around.
Her and the Question of What Counts as a Relationship
Spike Jonze wrote and directed Her in 2013. Joaquin Phoenix plays Theodore, a man going through a divorce who begins a relationship with an artificial intelligence named Samantha, voiced by Scarlett Johansson.
The film takes place in a near-future Los Angeles. The technology is plausible enough that the central premise feels possible rather than absurd. Theodore talks to Samantha through an earpiece. She learns and grows. She develops feelings, or something close to them.
Their relationship is unconventional by any measure. She has no body. She exists as software. Yet the emotional beats of their connection follow patterns that any viewer can recognise. They flirt. They argue. They grow apart.
Her does not settle the question of whether a relationship with an AI can be real. It shows that the feelings involved are real enough to the person having them.
Closing Observations
These films share a willingness to sit with ambiguity. They do not resolve neatly. The relationships they depict are messy, conditional, and sometimes exploitative. They ask viewers to consider arrangements that fall outside traditional frameworks and to find the humanity in them anyway.
Anora and Shiva Baby represent recent additions to this category, both made by young filmmakers with distinct voices. The Graduate and Punch-Drunk Love come from different eras but carry similar concerns about alienation and connection. Her extends the question into speculative territory.
Each film earns its place by refusing to simplify what it depicts. The best movies about unconventional relationships treat their subjects as people rather than problems to be fixed.
