Movies Like 500 Days of Summer: 20 Romantic Picks to Watch

Movies like 500 Days of Summer are a source of valuable recreation for love buffs who find romantic fiction as soul-relaxing. 500 Days of Summer movie has various ups and downs in its plot, where characters observe peaks in love, romance, and closeness that often reflect sadistic events. The film remained successful in achieving positive reviews and critical remarks.

We have picked a romantic story that perfectly blends love and strangeness in relationships. Filmic scenes provide flashbacks of previous close ties that ultimately left some remarkable memories. Get ready to enjoy more twists by delving into more similar genres.

Movie Name500 Days of Summer
DirectorMarc Webb
ProducerMason Novick
Release DateJanuary 17, 2009
Running Time95 minutes
Production CompanyDune Entertainment
Distributed ByFox Searchlight Pictures
Budget Allocate$7.5 million
Box Office Hit$60.7 million

500 Days of Summer (2009) Plot

The plot unveils the story of Tom (played by Joseph Gordon-Levitt), a writer of greeting cards who works for the same company. Summer (Zooey Deschanel) is a girl employed by the same company. They often discuss different topics, and music is one of them. They also talk about love, but Summer is less conscious than Tom.

Tom and Summer finally delve into relations, becoming famous among their colleagues. After some time, they start arguing on different occasions due to misunderstandings. Summer (Zooey Deschanel) unexpectedly breaks up with him. He reviews their 500 days together, searching for where things went wrong, and in the process, Tom rekindles his genuine passions in life.

500 Days of Summer (2009)

Box Office Collection

United States & Canada$32.4 million
United Kingdom$1.9 million

20 Movies Like 500 Days of Summer (2009)

Below is the complete romantic comedy package that provides 500 Days of Summer movies like stories through further picks. Whether you are a comedy lover or have a romantic touch in your cinematic taste, go with this cinematic album!

Garden State (2004)

Movie NameGarden State (2004)
DirectorZach Braff
ProducerGary Gilbert
Release DateJanuary 16, 2004
Running Time102 minutes
Production Budget$2.5 million
Film Revenue$35.8 million

Garden State (2004) is a romantic love story-based movie directed by Zach Braff. The movie focuses on Andrew Largeman (Braff), a 26-year-old actor/waiter returning to his New Jersey hometown following his mother’s passing. Braff drew inspiration for the film from his life encounters.

After years away, Andrew Largeman (played by Zach Braff), a bit part actor on TV, comes back to his small New Jersey hometown for his mother’s funeral. He faces his old life, including his bossy dad (Ian Holm). He meets Sam (Natalie Portman), a fibber and music enthusiast, and they hit it off. With old acquaintances, Largeman patches up old hurts and makes new friends.

Garden State (2004)

La La Land (2016)

Movie NameLa La Land (2016)
DirectorDamien Chazelle
ProducerFred Berger
Release DateAugust 31, 2016
Running Time128 minutes
Production Budget$30 million
Film Revenue$447 million

La La Land (2016) is a romantic dramatic film based on a relationship directed by Damien Chazelle. Ryan Gosling and Emma Stone headline the film as a jazz pianist and an aspiring actress who cross paths and develop a romance while chasing their aspirations in Los Angeles. Rosemarie DeWitt, John Legend, J. K. Simmons, and Finn Wittrock are joining them in the supporting cast.

Sebastian (played by Ryan Gosling) and Mia (Emma Stone) are brought together by their shared passion for pursuing their dreams. However, as they achieve success, they encounter choices that strain their relationship, and the dreams they cherished in each other start to strain their bond.

La La Land (2016)

High Fidelity (2000)

Movie NameHigh Fidelity (2000)
DirectorStephen Frears
ProducerTim Bevan
Release DateMarch 17, 2000
Running Time113 minutes
Production Budget$30 million
Film Revenue$47.1 million

High Fidelity (2000) is a novel-based depiction of the romantic drama film. Adapted from Nick Hornby’s 1995 British novel of identical title, the film relocates its setting from London to Chicago and alters the protagonist’s name while retaining the essence of the story.

Rob Gordon (played by John Cusack) runs a struggling record shop in Chicago, specializing in vinyl. Despite his deep knowledge and passion for music, his expertise doesn’t aid him when his girlfriend of many years, Laura (Iben Hjejle), leaves him. Reflecting on his past romantic failures and pursuit of happiness, Rob reluctantly faces the realities of adulthood.

High Fidelity (2000)

The Only Living Boy in New York (2017)

Movie NameThe Only Living Boy in New York (2017)
DirectorMarc Webb
ProducerAlbert Berger
Release DateAugust 11, 2017
Running Time88 minutes
Film Revenue$2.1 million

The Only Living Boy in New York (2017) is a romantic drama movie directed by Marc Webb. Following his college graduation and relocation to an apartment, Thomas Webb strikes up an unlikely friendship with a neighbor who drinks heavily but offers insightful advice alongside shots of whiskey. 

However, Thomas’s world shatters when he discovers his father’s affair with a captivating woman. Driven to end the affair, Thomas ends up in bed with her, setting off a series of events that will upend his understanding of his family and himself.

The Only Living Boy in New York (2017)

My Best Friend’s Wedding (1997)

Movie NameMy Best Friend’s Wedding (1997)
DirectorP. J. Hogan
ProducerJerry Zucker
Release DateJune 20, 1997
Running Time104 minutes
Production Budget$38 million
Film Revenue$299.3 million

My Best Friend’s Wedding (1997) film is a blend of romance and comedy directed by P.J. Hogan. The plot narrates the story in which longtime friends Julia Roberts and Dermot Mulroney planned to marry if they were single by 28. Just before Julianne’s 28th birthday, Michael reveals he’s marrying a stunning 20-year-old, Kimberly (Cameron Diaz). 

Realizing her true feelings too late, Julianne resolves to halt the wedding. But complications arise when she’s named maid of honor, making her mission even trickier. It is one of the ideal movies like (500) Days of Summer.

My Best Friend's Wedding (1997)

10 Things I Hate About You (1999)

Movie Name10 Things I Hate About You (1999)
DirectorGil Junger
ProducerAndrew Lazar
Release DateMarch 31, 1999
Running Time97 minutes
Production Budget$13 million
Film Revenue$60.4 million

10 Things I Hate About You (1999) film is a lovely depiction of liking and disliking relationships. In this plot story, Kat Stratford (Julia Stiles) is stunning, intelligent, and often off-putting to her peers, resulting in few suitors. 

For complicating matters, household regulations dictate that her younger sister, Bianca (Larisa Oleynik), can’t date until Kat does, prompting efforts to arrange a romance for the reluctant Kat. Then, Kat encounters the charismatic newcomer Patrick Verona (Heath Ledger). It is one of the best movies like 500 Days of Summer.

10 Things I Hate About You (1999)

The Breakup (2006)

Movie NameThe Breakup (2006)
DirectorPeyton Reed
ProducerVince Vaughn
Release DateJune 2, 2006
Running Time105 minutes
Production Budget$52 million
Film Revenue$205.7 million

The BreakUp (2006) is a romantic comedy film that is one of the similar movies like 500 Days of Summer. Jay Lavender and Jeremy Garelick penned the screenplay based on a story they crafted alongside Vaughn. Universal Pictures handled the film production.

Brooke (Jennifer Aniston), an art dealer, and Gary (Vince Vaughn), a trip-bus driver, reach the end of their relationship but can’t decide who should leave their shared condo. Despite friends’ suggestions of sneaky tactics, neither Brooke nor Gary budge. The only option left is to become adversaries under one roof.

The Breakup (2006)

50/50 (2011)

Movie Name50/50 (2011)
DirectorJonathan Levine
ProducerEvan Goldberg
Release DateSeptember 12, 2011
Running Time100 minutes
Production Budget$8 million
Film Revenue$41.1 million

50/50 (2011) is another romantic film that narrates an interesting story with humor and seriousness. The plot unveils Adam Lerner (Joseph Gordon-Levitt) has prioritized his health, identifying the malicious tumors to his spine particularly devastating. 

Adam wants to remain positive despite negative reactions from his mother (Anjelica Huston) and friend Kyle (Seth Rogen). Seeking support, Adam begins therapy with Dr. Katherine McKay (Anna Kendrick), but their dynamic blurs the line between professional and personal.

Drawing loose inspiration from Reiser’s encounter with cancer, Rogen’s character, Kyle, mirrors aspects of Rogen’s personality. Production took place from February to March 2010. “50/50” premiered on September 30, 2011, accumulating $41 million in box office revenue. The film garnered acclaim, especially for Gordon-Levitt’s acting and Reiser’s script.

5050 (2011)

The Spectacular Now (2013)

Movie NameThe Spectacular Now (2013)
DirectorJames Ponsoldt
ProducerTom McNulty
Release DateJanuary 18, 2013
Running Time95 minutes
Production Budget$2.5 million
Film Revenue$6.9 million

The Spectacular Now (2013) is a romantic drama movie directed by James Ponsold. Debuting at the 2013 Sundance Film Festival, The Spectacular Now hit theaters in the United States on August 2, 2013, amassing critical acclaim and over $6 million in global box office earnings. The film earned two nominations internationally.

Sutter, known for his wild partying, crosses paths with introverted Aimee after a drunken night ends on a stranger’s lawn. While Sutter navigates his issues, Aimee contemplates life after school. Surprisingly, a romance sparks between them amidst their divergent paths.

The Spectacular Now (2013)

Silver Linings Playbook (2012)

Movie NameSilver Linings Playbook (2012)
DirectorDavid O. Russell
ProducerDonna Gigliotti
Release DateSeptember 8, 2012
Running Time122 minutes
Production Budget$21 million
Film Revenue$236.4 million

Silver Linings Playbook (2012) is a romantic film that debuted at the 2012 Toronto International Film Festival on September 8, 2012, followed by its release in the United States on November 16, 2012. Following job loss and marital breakdown, Pat Solatano (Bradley Cooper) finds himself residing with his parents (Robert De Niro and Jacki Weaver) after a stint in a mental institution. While he aims to rebuild and reconcile with his wife, his parents hope he’ll join their enthusiasm for the Philadelphia Eagles. 

Complexity arises when Pat encounters Tiffany (Jennifer Lawrence), who proposes aiding his reconciliation in exchange for a significant favor. The film received widespread acclaim, particularly for Russell’s direction and the standout performances of Cooper and Lawrence. It accumulated $236.4 million in global box office revenue.

Silver Linings Playbook (2012)

Eternal Sunshine of the Spotless Mind (2004)

Movie NameEternal Sunshine of the Spotless Mind (2004)
DirectorMichel Gondry
ProducerSteve Golin
Release DateMarch 19, 2004
Running Time108 minutes
Production Budget$20 million
Film Revenue$74 million

Eternal Sunshine of the Spotless Mind (2004) is a science fiction movie based on dramatic fantasy and romance. Following a heartbreaking split, Clementine (Kate Winslet) opts for a memory erasure procedure to erase ex-boyfriend Joel (Jim Carrey) from her mind. Upon learning of Clementine’s drastic measures, Joel decides to undergo the same process, gradually losing memories of his beloved. 

Directed by Michel Gondry, the visually captivating film delves into the complexity of relationships and the anguish of letting go. It is one of the romance movies like 500 Days of Summer.

Eternal Sunshine of the Spotless Mind (2004)

Don Jon (2013)

Movie NameDon Jon (2013)
DirectorJoseph Gordon-Levitt
ProducerRam Bergman
Release DateJanuary 18, 2013
Running Time90 minutes
Production Budget$7.5 million
Film Revenue$41.3 million

Don Jon (2013) is a romantic-comedy-drama film that describes the story of Bartender Jon Martello (Joseph Gordon-Levitt) from New Jersey, who has his priorities straight: friends, family, car, church, and sexual exploits. He’s an intercourse addict with no real connections to women. 

Bartender’s approach until he encounters Barbara (Scarlett Johansson), who challenges his usual approach. Jon embarks on his first genuine courtship, but his fixation on erotica jeopardizes everything.

Under its initial title, Don Jon’s Addiction, the film premiered at the Sundance Film Festival on January 18, 2013. Its United States release followed on September 27, 2013. With a global box office revenue of $41 million, the film garnered mostly reviews from critics.

Don Jon (2013)

Gigantic (2008)

Movie NameGigantic (2008)
DirectorMatt Aselton
ProducerMindy Goldberg
Release DateSeptember 8, 2008
Running Time98 minutes
Film Revenue$165,888

Gigantic (2008) is a funny film narrating the story of Brian Weathersby (Paul Dano), a mattress salesman overshadowed by his accomplished siblings who crave a more fulfilling existence. Opting to adopt a child, he encounters peculiar happenings.

Brian feels he’s being pursued, and the atypical daughter of a client, Harriet “Happy” Lolly (Zooey Deschanel), starts appearing unexpectedly. Juggling potential fatherhood preparations and managing Happy’s domineering father, Al (John Goodman), Brian faces an unpredictable journey.

Inspired by Aselton’s childhood desire for her parents to adopt a Chinese infant, the narrative unfolds against the backdrop of New York and Connecticut. Premiering at the 2008 Toronto International Film Festival, the movie hit theaters in the United States on April 3, 2009.

Gigantic (2008)

Swingers (1996)

Movie NameSwingers (1996)
DirectorDoug Liman
ProducerVictor Simpkins
Release DateOctober 18, 1996
Running Time96 minutes
Production Budget$200,000
Film Revenue$4.6 million

Swingers (1996) is a romantic comedy film that earned critical acclaim and commercial success. Liman’s directorial debut also garnered him the Best New Filmmaker award at the 1997 MTV Movie Awards.

Mike Peters (Jon Favreau), a New Yorker adjusting to life in Los Angeles, grapples with advancing his comedy career while recovering from a recent breakup. Assisted by his friend Trent Walker (Vince Vaughn), a self-proclaimed ladies’ man, Mike learns the art of making connections and catching women’s interest. 

Gradually rebuilding his self-assurance, Mike encounters the charming and grounded Lorraine (Heather Graham), igniting a promising new relationship. Enjoy this movie if you are interested in (500) Days of Summer movies like stories.

Swingers (1996)

Celeste & Jesse Forever (2012)

Movie NameCeleste & Jesse Forever (2012)
DirectorLee Toland Krieger
ProducerJennifer Todd
Release DateJanuary 20, 2012
Running Time92 minutes
Production Budget$840,000
Film Revenue$3.6 million

Celeste & Jesse Forever (2012) is a romantic-comedy film that revolves around the childhood companions Celeste (Rashida Jones) and Jesse (Andy Samberg), who tied the knot early but find themselves growing apart.

A driven entrepreneur, Celeste contrasts with Jesse’s relaxed approach to life and career. Despite Celeste’s desire for divorce while maintaining the friendship, Jesse complies passively, though his love for her remains. Yet, as they confront the consequences of their split, Celeste starts to question her decision. It is one of the sad love movies like 500 Days of Summer.

Celeste & Jesse Forever (2012)

Her (2013)

Movie NameHer (2013)
DirectorSpike Jonze
ProducerMegan Ellison
Release DateOctober 12, 2013
Running Time126 minutes
Production Budget$23 million
Film Revenue$48.3 million

Her (2013) is a science fiction film that garnered universal critical acclaim, with special praise directed at the standout performances by Phoenix and Johansson. Despite a production budget of $23 million, the film amassed over $48 million in global box office earnings.

Theodore (Joaquin Phoenix), a tender-hearted individual who crafts personalized letters for clients, grapples with heartbreak following his divorce. Intrigued by a cutting-edge operating system touted to evolve into a distinct entity, Theodore initiates the program and encounters “Samantha” (Scarlett Johansson). Her vibrant voice exudes a blend of sensitivity and playfulness, drawing Theodore in. Initially forming a friendship, their connection swiftly blossoms into love.

Her (2013)

My Girl (1991)

Movie NameMy Girl (1991)
DirectorHoward Zieff
ProducerBrian Grazer
Release DateNovember 27, 1991
Running Time102 minutes
Production Budget$17 million
Film Revenue$121.5 million

My Girl (1991) is a romantic film set in Madison, Pennsylvania, during the summer of 1972, that follows the experiences of an 11-year-old girl. Its title pays homage to the iconic 1964 song by The Temptations, which is prominently featured in the film’s end credits.

Vada Sultenfuss (Anna Chlumsky), a tomboy with an unhappy disposition, carries the weight of her mother’s death during childbirth, compounded by her father’s (Dan Aykroyd) funeral business at home.

Misunderstood by her peers, especially with her closest friend Thomas J. Sennett (Macaulay Culkin), Vada faces additional challenges as she harbors a crush on her English teacher, Mr. Bixler (Griffin Dunne). Then, to find the answer to the query, How will an 11-year-old girl navigate such complexities? It is a fine portrayal of 500 Days of Summer like movies.

My Girl (1991)

Marriage Story (2019)

Movie NameMarriage Story (2019)
DirectorNoah Baumbach
ProducerDavid Heyman
Release DateAugust 29, 2019
Running Time137 minutes
Production Budget$18 million
Film Revenue$2.3 million

Marriage Story (2019) film is based on the dramatic portrayal of diverse relations in a romantic way. Announced in November 2017, the film swiftly assembled its cast during the same month. Production unfolded in New York City and Los Angeles from January to April of the following year. The plot unveils a theater director and his actress wife endure a challenging cross-country divorce that tests their limits, both personally and creatively.

Marriage Story (2019)

Yes Man (2008)

Movie NameYes Man (2008)
DirectorPeyton Reed
ProducerDavid Heyman
Release DateDecember 9, 2008
Running Time104 minutes
Production Budget$70 million
Film Revenue$223.2 million

Yes Man (2008) is a romance fiction movie about Carl Allen (Jim Carrey), who finds himself trapped in a cycle of negativity until he attends a self-help workshop that teaches the power of saying “yes” to life. Embracing this philosophy leads him to a series of remarkable and life-changing adventures: he earns a job promotion and discovers a new romantic connection. 

However, Carl soon realizes that excessive positivity, like anything else, can have drawbacks. It is one of the similar movies to watch if you like 500 Days of Summer.

Yes Man (2008)

Comet (2014)

Movie NameComet (2014)
DirectorSam Esmail
ProducerChad Hamilton
Release DateJune 13, 2014
Running Time91 minutes
Film Revenue$19,530

Comet (2014) is an American humor-cum-romanctic film directed by Sam Esmail. It is presented through fragmented glimpses of parallel universes and non-linear flashbacks; the film explores the complex dynamics within their relationship, showcasing its fluidity and evolution over time.

A skeptical young man (Justin Long) and a woman (Emmy Rossum) embark on a six-year relationship after a serendipitous encounter during a meteor shower. It is also one of the romantic movies like 500 Days of Summer.

Comet (2014)


Finally, the article ends with a note and hopes that viewers will get a charming look if they like romantic films. We have shortlisted the best possible stuff, which has been all-time classical. If you want to explore more movies like 500 Days of Summer, you must watch and enjoy these movies. Moreover, these movies contain sad events, humor, and love stories related to the diverse relations of characters.

Photo of author

Jordan Counsel

Jordan Counsel is a passionate movie enthusiast with a keen eye for cinematic details. With years of experience in the film world, Jordan brings a unique perspective to the art of movie analysis and critique. Whether dissecting the latest blockbuster or delving into the nuances of independent cinema, Jordan's writing provides readers with insightful and engaging content. When not glued to the silver screen, Jordan enjoys exploring the world of cinema, attending film festivals, and sharing recommendations for movie lovers everywhere.