10 Movies like 500 Days of Summer you must watch

By Romey Norton
Published: January 17, 2023 (Last updated: 3 weeks ago)

10 Movies like 500 Days of Summer you must watch. Got an itch after watching one of the great rom-com movies? Keep this list handy full of romantic comedy recommendations.

500 Days of Summer is the 2007 rom-com starring Joseph Gordon-Levitt and Zooey Deschanel and tells the story of Tom (Gordon-Levitt), who revisits the one year he shares with Summer (Deschanel).

Tom believed Summer was the one and wanted to spend his life with her. He goes back to unravel why and what went wrong. Summer has always professed she didn’t believe in relationships or “boyfriends,” so was this doomed from the start?

This film is a great conversation about relationships, expectations, and happiness. Tom’s character and happiness become dependent on Summer, and he loses himself because of that. This film is filled with themes of love, self-discovery, pain, and growth, all wrapped up in lighthearted comedy.  

10 Movies like 500 Days of Summer you must watch

The Perks of Being a Wallflower (2012) 

This beautiful coming-of-age story is based on the novel of the same name by Stephen Chbosky and follows the story of Charlie, a 15-year-old introvert’s life at high school. Charlie is very nervous about his new life and accidentally befriends some seniors, who embrace him, and this helps him cope with his haunting past. The Perks of Being a Wallflower has similar themes of love, self-discovery, a protagonist who is lost and trying to unravel and find reasons as to why, and navigating love and loss. It’s a special film with a stunning cast, one to watch.  

Crazy, Stupid, Love (2011) 

This film was a lot funnier than I first anticipated, and with a great cast and array of characters, it really delves into love and relationships. Cal, a middle-aged man, is heartbroken when his wife asks for a divorce. However, to get over his loss, he starts picking up women at a bar at the insistence of his new-found friend, Jacob. Jacob, a hot, sexy man, starts dating Cal’s daughter, and the film is worth watching for the party scene.  

La La Land (2017) 

Starring our two lovebirds from Crazy, Stupid, Love, Ryan Gosling, and Emma Stone come together with their great chemistry for this movie musical. When Sebastian, a pianist, and Mia, an actress, follow their passion and achieve success in their respective fields, they find themselves torn between their love for each other and their careers. This film has the heart-breaking similarity of a struggling relationship, and how people must make compromises if they’re willing to make a relationship work.  

High Fidelity (2000) 

Here is an example of a 2000’s indie film like 500 days of Summer, as its story surrounds a love that was never meant to be. Adapted from Nick Hornby’s book by the same name, we see our protagonist Rob Gordon go down memory lane to tell us about the top five breakups of all time. The audiophile record store owner is certainly unlucky in love, and with a friend, they investigate the reasons behind his failures to find true love.  

Eternal Sunshine of the Spotless Mind (2004) 

This film is a seriously good watch and centers around two completely opposite characters in a relationship, and their conflicting personalities lead to a bad breakup. Joel (Jim Carrey) is a warm, introverted person, and Clementine (Kate Winslet) is free-spirited and unpredictable. Clementine undergoes a procedure to erase him from her memory, and Joel does the same. However, Joel realizes he doesn’t want to lose these memories as he still loves her. The film is filled with the unforgettable experiences he had with Clementine and their relationship.  

Blue Valentine (2010)  

This film is another example of people who were once madly in love, and the breakdown of their relationship. After a classic meet-cute and accidental pregnancy, Dean and Cindy get married young in their life. Over time, every mundane morning, their life begins with frustrating and unresolved confrontations as they attend to the daily needs of their six-year-old daughter. 

One Day (2011) 

Each year Dexter and Emma, who first meet during their graduation in 1988, keep the date July 15th free to meet up and catch up. The film follows what they do on July 15 annually, and their tragic love story. Based on the beloved book, this film is beautifully filmed and performed.  

Before We Go (2014) 

This sweet romantic-drama film has a big heart and is focused on how people can heal and grow a relationship, and deals with themes of love, loss, confronting fears, and connection. The story surrounds Nic and Brooke, who meet one night in the subway after Brook misses her last train home. The two confide in one another, confronting their life-long fears. 

Silver Linings Playbook (2012) 

A strong film, going slightly away from the rom-com genre slightly and into the more serious, Silver Linings Playbook is a drama-romance film starring Jennifer Lawrence and Bradley Cooper, as two people with broken relationships (through abuse and death) and mental health issues, trying to be better and Pat wishes to reconcile with his ex-wife. This is a film about relationships, navigating life, disarray, depression, and isolation, and is an emotional rollercoaster.  

How to Lose a Guy in Ten Days (2003) 

This film is one of my personal favorites, and it’s making the list for its comedy, its romance, and its struggles between finding love, keeping love, and wanting to progress and develop in your career. An advice columnist, Andie Anderson (Kate Hudson), tries pushing the boundaries of what she can write about in her new piece about how to get a man to leave you in 10 days. At the same time, Benjamin a sports Journalist, is challenged by his co-workers to make a woman fall in love with him, they both meet, and whilst each play one another, they fall for one another, but is that enough when they discover each other’s agendas?  

And that concludes our 10 Movies like 500 Days of Summer list. What’s your favorite from this list? Comment below.

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