Love is not always a fairy tale, and no movie captures that quite as well as 500 Days of Summer. It is raw, real, and full of scenes that have you smiling one minute and shattering your heart the next. If you enjoy movies like 500 Days of Summer, where romance is not just about happily-ever-after's but the beautiful, messy chaos in between, then you are in for a treat!

What if you could erase heartbreak like in Eternal Sunshine of the Spotless Mind? Or lose yourself in a romantic dream like La La Land? Maybe you are in the mood for the steamy chemistry of The Notebook or the carefree fun of Nick & Nora’s Infinite Playlist. No matter what, this list of must-watch movies will sweep you on an emotional ride in ways that will stick with you!

13. The Break-Up 

Breakups are never easy, but what happens when neither person is willing to move out? The Break-Up follows Jennifer Aniston and Vince Vaughn playing a couple stuck together in the same condo after splitting up, turning their once-loving relationship into a hilarious, petty warzone. Between passive-aggressive tricks, tantrums, and emotional standoffs, this film perfectly captures the messy aftermath of love gone wrong.  

As with 500 Days of Summer, The Break-Up is not afraid to get real about relationships. It strips away the romance, revealing the aggravation, the pain, and the lingering attachment that makes it so hard to move on. The movie walks a fine line between humor and heartbreak, making it a relatable watch for anyone who has ever been through a love story that did not end in a fairytale. 

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12. My Best Friend’s Wedding

In My Best Friend’s Wedding Julia Roberts stars as Julianne, a woman who finds herself in love with her best friend—just days before his wedding. What follows is a storm of sabotage attempts, hilarious mishaps, and painful realizations as she tries to win him over. It is a rom-com with just the right amount of heartache to keep things interesting.  

This movie like 500 Days of Summer, is all about the wrong timings. Love does not always arrive when it is supposed to, and sometimes, you may not appreciate what you have until it is slipping away. If you love stories that mix romance with raw emotions and a bittersweet ending, this one is for you!  

11. Celeste and Jesse Forever

Can exes really stay friends? Celeste played by Rashida Jones and Jesse played by Andy Samberg are a divorced couple who still hang out like best friends, well until one of them gets the jump on moving on. Suddenly, the reality of their breakup comes crashing down on them, and they are forced to go through the aching transition from lovers to strangers.  

Celeste and Jesse Forever echoes the emotional rollercoaster of 500 Days of Summer, revealing that just because two people love each other does not mean they are meant to be. It is an honest, funny, and sometimes painful look at how relationships evolve and how difficult it is to truly let go.  

10. The Spectacular Now

Young love is not always easy, and The Spectacular Now is proof. Sutter played by Miles Teller is a charming but aimless high school senior who finds himself falling for the quiet and thoughtful Aimee played by Shailene Woodley. As their relationship grows, Sutter struggles with his own fears and insecurities, creating an emotionally charged coming-of-age romance.

Similar to 500 Days of Summer, this movie presents an authentic depiction of love—unpredictable, messy, and at times painful. It does not rely on fairytale clichés but instead shows the reality of two people trying to figure out who they are while navigating a relationship that may or may not last forever.  

9. High Fidelity

What better way to get over a breakup than by making a breakups list? In High Fidelity John Cusack’s character, Rob, will take you on a trip down memory lane through his previous relationships, as he tries to figure out where it all went wrong. With humor, self-reflection, and a killer soundtrack, this movie is a timeless breakup classic! 

Like 500 Days of Summer, High Fidelity embraces the nonlinear storytelling, leaping between flashbacks to reconstruct the narrative of a love affair gone wrong. It is introspective, witty, and may be cringingly familiar to anyone who has ever spent hours dissecting their own love lives to the tune of melancholic indie ballads.

8. Before Sunset

What if you got a second chance with the one that got away? Before Sunset brings Jesse played by Ethan Hawke and Céline played by Julie Delpy back together nine years after their short but passionate affair. Now older and wiser, they spend an afternoon wandering through Paris, questioning love, life, and the decisions they made.  

This movie has the same raw, thought-provoking conversations that made 500 Days of Summer so special. It is  intimate, realistic, and comes with a reminder that love is often about timing—and sometimes, the timing just is not right. 

7. Marriage Story

If 500 Days of Summer was about love fading, Marriage Story is about its devastating breakdown. Scarlett Johansson and Adam Driver star as a couple navigating a messy divorce, struggling to separate their shared past from the harsh legal battle unfolding in front of them. Like Tom and Summer, this couple starts with love and ends with something much more complicated.

Marriage Story is harshly realistic about how even the deepest love can dissolve when life gets in the way, making it one of the most emotionally gripping break-up movies of all time!

6. Her

Love does not always appear as one  would imagine. In Her, Joaquin Phoenix plays a lonely writer who falls for his AI assistant, voiced by Scarlett Johansson. What begins as an unusual romance becomes a deep examination of connection, intimacy, and what it means to truly love someone—or in this case something.  

Like 500 Days of Summer, Her challenges traditional romance, revealing the beauty and pain of love in an intensely personal manner. It is a poetic, visually breathtaking movie that will leave you contemplating relationships long after the credits are rolling.  

 5. The Notebook

Few love stories are as passionate, or as heartbreaking, as Noah and Allie’s. From summer romance to years of separation, The Notebook stars Ryan Gosling and Rachel McAdams who recite a sweeping love story filled with grand gestures and teary moments. But in the midst of the romance, there lies a story about choices, regrets, and the ability of love to stand strong.

While 500 Days of Summer explored love’s fleeting nature, The Notebook peeks into the possibilities of what happens when love simply refuses to fade. It offers a fresh perspective on romance—something Hollywood already has in abundance—but still captures the intense emotions making it a timeless romantic classic to date!

4. Eternal Sunshine of the Spotless Mind

What if you could wipe out all the painful memories of your ex? Jim Carrey and Kate Winslet play a couple who go through a procedure to erase each other from their minds—only to discover that some love is impossible to forget. Eternal Sunshine of the Spotless Mind bends reality while delivering a heart-wrenching look at love and loss.  

Like 500 Days of Summer, this movie plays with nonlinear storytelling, forcing you to piece together the love story as it unravels. It is visually stunning, emotionally devastating, and a must-watch for anyone who has ever wished they could erase an ex!

3. Nick & Norah’s Infinite Playlist

One night. One city. One epic indie music-fueled adventure. Michael Cera and Kat Dennings star as strangers who team up for a night of mischief, music, and unexpected romance. It is offbeat, charming, and full of heart—just right for fans of 500 Days of Summer's quirky appeal.

Like Tom and Summer, the story of Nick and Norah is also unpredictable, full of awkward encounters and true connection. It is a feel-good love story with just the right amount of emotional depth.  

2. La La Land

Love and dreams are not always meant to go together, and La La Land is proof. Ryan Gosling and Emma Stone star as wannabe artists who see their crazy-in-love relationship challenged by ambition, timing, and the shifting course of life.

Like 500 Days of Summer, this film captures the reality that not all love stories are destined to be forever—but that does not mean they were not real! 

1. Silver Linings Playbook

Bradley Cooper and Jennifer Lawrence bring in this crazy energy and undeniable chemistry to this story of love, healing, and second chances. Silver Linings Playbook is a deep rom-com. Unlike most rom-coms, it does not shy away from the struggles of mental health and emotional baggage, instead it embraces them with honesty and heart. Very much uch like 500 Days of Summer, this film does not offer a sugar-coated version of love. It is messy, unpredictable, and filled with imperfect moments—just like real relationships.

These movies like 500 Days of Summer do not just narrate a story—they let you experience each moment of it, from the exhilaration of being in love to the pain of letting go. If you are in the mood for a movie that tugs at your heartstrings, why not start with one from this list? So grab your snacks, get comfy, press play, and let yourself feel every second!

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Which of these movies hit you the hardest? Or is there a secret gem we missed? Let us know in the comments below!