10 Of The Best Movies About Being Single

In this romantic comedy-drama, 500 Days of Summer takes the audience through a rollercoaster of emotions as experienced in a casual relationship between a greeting card writer and their co-worker. The film is a captivating story with a nonlinear narrative structure as written by Scott Neustadter and Michael H. Weber and directed by Marc Webb. It stars Joseph Gordon-Levitt and Zooey Deschanel. 

The film explores the complexities of love and heartbreak through the memories of a failed relationship. Despite being an independent production, it became a sleeper hit, earning over $60 million worldwide on a $7.5 million budget. It received critical acclaim, winning Best Original Screenplay at the Satellite Awards and Best Screenplay at the Independent Spirit Awards. 500 Days of Summer is hailed as a standout film of 2009, drawing comparisons to beloved classics like Annie Hall and High Fidelity (one of which happens to also appear further down on this list).

Eternal Sunshine of the Spotless Mind is the brainchild of Charlie Kaufman, Michel Gondry, and Pierre Bismuth, with Kaufman writing the final screenplay and Gondry directing the feature. It stars Jim Carrey in a surprisingly serious and raw performance as the film’s main character, Joel. Kate Winslet plays Clementine, Joel’s ex, and the total antithesis of who Joel is. 

Eternal Sunshine is a surreal adventure with a sci-fi twist about a man who finds out that his ex-girlfriend has used a secret technology to erase him from her memories, so he undergoes the same procedure to erase her from his. The bulk of the film takes place after Joel changes his mind at the last minute, but it’s already too late, so he must helplessly watch as his memories are being erased. The audience comes along on a journey of romance, heartbreak, and eventual closure as Joel relives his past with Clementine one last time before it’s gone forever.

The Lobster, a 2015 absurdist black comedy-drama, takes viewers on a bizarre journey into a dystopian world. If Eternal Sunshine of the Spotless Mind has elements of surrealism laced into it, The Lobster is completely drenched with surreal elements. Directed by Yorgos Lanthimos, the film features an impressive ensemble cast, including Colin Farrell, Rachel Weisz, and John C. Reilly. 

The story revolves around a newly single man who must find a romantic partner within 45 days at a peculiar hotel or face being transformed into an animal. Premiering at the Cannes Film Festival, The Lobster competed for the Palme d’Or and won the Jury Prize. It garnered positive reviews for its screenplay, humor, and thematic content, earning nominations at prestigious award ceremonies such as the Academy Awards and the British Academy Film Awards.

Frances Ha is a delightful comedy-drama that follows a young woman in New York as she pursues her dreams of joining a dance company, even as the odds seem to stack against her. Directed by Noah Baumbach and co-written by Baumbach and Greta Gerwig (who also stars as the lead), the film intentionally embraces a black-and-white visual style. Premiering at the Telluride Film Festival on September 1, 2012, it later received a limited theatrical release in the United States on May 17, 2013, courtesy of IFC Films.

Frances Ha delivers a poignant message that the journey of self-discovery is an ongoing process. It highlights the notion that one’s path may differ from others and take longer to unfold, but that doesn’t make it any less valuable or fulfilling.

Her is a remarkable 2013 science-fiction romantic drama directed by Spike Jonze, marking his solo screenwriting debut. The story centers around Theodore Twombly (Joaquin Phoenix), who forms a unique relationship with Samantha, an artificial intelligence virtual assistant (voiced by Scarlett Johansson). Supported by a talented cast including Amy Adams and Rooney Mara, Her explores themes of love, loneliness, and the evolving nature of human connections.

Premiering at the 2013 New York Film Festival, the film garnered widespread acclaim for Phoenix and Johansson’s performances and Jonze’s screenplay and direction. It received multiple award nominations and won the Academy Award for Best Original Screenplay. Her‘s thought-provoking narrative, and captivating performances make it a standout film of its time.

The Break-Up, a 2006 American romantic comedy-drama directed by Peyton Reed, offers a humorous and relatable exploration of the complexities of relationships and the challenges of navigating the aftermath of a breakup. Starring Vince Vaughn and Jennifer Aniston, the film tells the story of a couple who decide to end their relationship but find themselves caught in a series of amusing and often frustrating situations as they continue to live together in the same apartment. 

With its blend of comedy and heartfelt moments, The Break-Up provides an entertaining and honest portrayal of the ups and downs of love and singledom. Produced by Universal Pictures, the film showcases the talents of its lead actors and delivers a satisfying blend of laughter and emotional resonance.

The Apartment, a 1960 American romantic comedy-drama directed by Billy Wilder, remains a cinematic masterpiece and accredited classic. Starring Jack Lemmon and Shirley MacLaine, it follows an insurance clerk who allows his superiors to use his apartment for sexual affairs with the hope that it will somehow advance his own career. When he meets Fran Kubelik (MacLaine), C.C. Baxter (Lemmon) finds himself drawn to her, unaware that she is involved with his boss. 

The movie achieved massive critical acclaim and commercial success, earning 10 Academy Award nominations and winning five, including Best Picture and Best Director. Regarded as one of the greatest films ever made, The Apartment continues to captivate audiences with its brilliant performances, compelling story, and exploration of complex relationships.

Obvious Child, a 2014 American romantic comedy-drama, boldly tackles the topic of abortion with wit and authenticity. Written and directed by Gillian Robespierre in her directorial debut, the film stars Jenny Slate as Donna, a stand-up comedian who faces an unexpected pregnancy after a drunken one-night stand. Determined to remove the stigma surrounding abortion, Robespierre crafted a poignant story that challenges misrepresentations of unplanned pregnancy. 

Premiering at the Sundance Film Festival in 2014, Obvious Child garnered critical acclaim for its honest portrayal of abortion, receiving accolades from the National Board of Review and Independent Spirit Awards. The film’s realistic humor and thought-provoking narrative offer a refreshing and meaningful perspective on a sensitive subject.

Sleepless in Seattle is a beloved romantic comedy-drama directed by Nora Ephron. Starring Tom Hanks and Meg Ryan, the film tells the story of a journalist who falls for a recently widowed architect after his son calls into a radio show seeking a new partner for his grieving father. Despite not meeting until the end, their connection captivates audiences. Inspired by An Affair to Remember, the script went through revisions to infuse humor after many studios rejected it for being just a drama. 

Released to positive reviews, it became a surprise commercial hit, grossing over $227 million worldwide and engaging with audiences who could relate to both characters’ experiences as single Americans seeking a partnership. Sleepless in Seattle remains a classic in the romantic comedy genre and solidified Ephron’s reputation as a talented filmmaker.

Annie Hall is a renowned satirical romantic comedy-drama directed by Woody Allen. Allen stars as Alvy Singer, a man reflecting on the reasons for the failure of his relationship with Annie Hall, played by Diane Keaton in a role written specifically for her. The film, shot in New York City and Los Angeles, introduced a new level of seriousness for Allen as it delves into themes of self-discovery, the nature of love, and the challenges of sustaining a romantic partnership. While the film doesn’t focus solely on the experience of being single, it offers a poignant exploration of relationships and personal growth.

Annie Hall garnered critical acclaim, winning four Academy Awards, including Best Picture, and four BAFTA awards. Ranked among the greatest films ever made, Annie Hall is celebrated for its screenplay and remains a beloved favorite in Woody Allen’s filmography.