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100+ Movies like (500) Days of Summer

3.6
2009 Comedy, Drama, Romance

Explore movies similar to (500) Days of Summer, a romantic comedy-drama that follows the ups and downs of Tom Hansen's relationship with Summer Finn. The film chronicles their initial attraction, casual dating phase, and Tom's eventual heartbreak when Summer ends their relationship, revealing her disbelief in true love. With themes of unrequited love, self-discovery, and moving on after heartbreak, this page curates a selection of movies that delve into the complexities of modern romance, offering relatable narratives and emotional journeys akin to Tom's bittersweet experience.

Made of Honor

Made of Honor

3.2
2008

Both "Made of Honor" and "(500) Days of Summer" follow a similar narrative arc of a man falling for a woman who is hesitant about commitment. In "(500) Days of Summer", Tom falls for Summer but she does not believe in true love, leading to their eventual breakup. Similarly in "Made of Honor", Tom realizes his love for his best friend Hannah but she gets engaged to another man, Colin. The movies explore the themes of unrequited love, the challenges of modern relationships, and the protagonist's journey to find fulfillment. The protagonists, Tom in both films, go through emotional turmoil and heartbreak before ultimately gaining clarity about what they truly want in a partner. The movies parallel each other in their portrayal of the complexities of love and the difficulties of navigating relationships in the modern era.

They Came Together

They Came Together

2.8
2014

"They Came Together" is a parody that satirizes the romantic comedy genre, drawing heavy parallels to "(500) Days of Summer". Both films follow a non-linear narrative structure, depicting the ups and downs of a romantic relationship between two people with contrasting views on love. The male protagonists, Tom and Joel, are hopeless romantics who fall for women, Summer and Molly, who are more cynical and commitment-averse. The relationships start off casual but the men develop deeper feelings, leading to conflicts and eventual breakups when their expectations clash with their partners' lack of desire for a serious commitment. The films explore themes of idealized love versus reality, self-delusion, and the pain of heartbreak. They also feature quirky supporting characters, pop culture references, and a bittersweet ending where the protagonists gain perspective and move on, leaving open the possibility of finding true love with someone else.

Palm Trees and Power Lines

Palm Trees and Power Lines

3.2
2023

Both "Palm Trees and Power Lines" and "(500) Days of Summer" explore unconventional romantic relationships that ultimately end in heartbreak for the protagonist. In "(500) Days of Summer", Tom falls for Summer despite her reluctance to commit, while in "Palm Trees and Power Lines", the teenage Lea is groomed into a sexual relationship with the much older Tom. Both protagonists are blinded by their feelings and overlook red flags, only realizing the incompatibility later. The movies depict the emotional turmoil of one-sided relationships and the pain of unrequited love. They also touch on themes of disillusionment, growing up, and moving on from failed relationships.

Kissing Jessica Stein

Kissing Jessica Stein

3.0
2002

Both "Kissing Jessica Stein" and "(500) Days of Summer" follow a similar narrative arc of an unconventional romantic relationship that ultimately does not work out. In "(500) Days of Summer", Tom falls for Summer despite her not believing in true love, and they have a casual relationship that grows deeper before Summer ends it, leaving Tom heartbroken. In "Kissing Jessica Stein", Jessica unexpectedly starts dating Helen after responding to her personal ad, and they have a passionate relationship that Jessica struggles to fully commit to, leading to their breakup when Jessica cannot give Helen the intimacy she needs. The movies parallel each other in depicting the ups and downs of relationships that challenge the protagonists' preconceived notions about love, forcing them to re-evaluate their perspectives on romance and relationships by the end.

Daria in 'Is It Fall Yet?'

Daria in 'Is It Fall Yet?'

3.6
2000

Both "Daria in 'Is It Fall Yet?'" and "(500) Days of Summer" explore the complexities of romantic relationships and the challenges of navigating unrequited love and heartbreak. The central characters, Tom and Daria, experience relationships that do not work out due to mismatched expectations and incompatibilities with their partners, Summer and Tom respectively. The movies parallel each other in depicting the emotional turmoil and self-discovery that follows a breakup, as Tom and Daria grapple with feelings of rejection and disillusionment. However, they ultimately find solace in redefining their perspectives on love and moving forward with renewed purpose. The movies also touch on themes of identity, with Jane and Quinn undergoing crises that mirror the protagonists' journeys of self-reflection after their relationships end. Overall, the movies share a poignant exploration of the bittersweet nature of love and the resilience of the human spirit in overcoming heartache.

Dinner with Friends

Dinner with Friends

2.7
2001

Both "Dinner with Friends" and "(500) Days of Summer" explore the complexities and challenges of romantic relationships, particularly the dissolution of a relationship. In "(500) Days of Summer", Tom's relationship with Summer follows a similar arc to Tom and Beth's marriage in "Dinner with Friends" - starting with passion and optimism, but gradually deteriorating due to incompatibilities and differing expectations. The movies depict the emotional turmoil and heartbreak experienced when a relationship ends, as well as the impact it has on the couple's close friends. They also touch on themes of self-discovery, moving on after a breakup, and the search for true love and happiness. The non-linear storytelling in "(500) Days of Summer" parallels the flashbacks in "Dinner with Friends" that provide insight into the relationships' origins and evolution over time.

The Five-Year Engagement

The Five-Year Engagement

2.9
2012

Both "The Five-Year Engagement" and "(500) Days of Summer" follow the ups and downs of a romantic relationship between two people with differing perspectives on love and commitment. In "(500) Days of Summer", Tom believes in true love while Summer is more casual about relationships, leading to their eventual breakup. Similarly in "The Five-Year Engagement", Tom wants to get married while Violet keeps delaying their wedding due to her career ambitions, straining their relationship over time. The movies parallel each other in showing how mismatched expectations and priorities can derail a relationship, even when the couple cares deeply for each other. Both films also depict the male protagonist's emotional journey of heartbreak, disillusionment, and eventual growth after the breakup, before finding hope for new love in the end.

Friends with Benefits

Friends with Benefits

3.3
2011

Both "Friends with Benefits" and "(500) Days of Summer" follow a similar narrative arc of two friends who develop romantic feelings for each other and engage in a casual sexual relationship, only to realize they want something more serious. The protagonists, Tom and Dylan, initially believe they can keep things casual and avoid emotional attachment, but their feelings grow deeper over time. The relationships are complicated by the female leads, Summer and Jamie, being more hesitant about commitment. There are moments of miscommunication and misunderstanding that strain the relationships. Ultimately, the male leads come to terms with their desire for true love and make grand romantic gestures to win back the women they love, realizing their initial beliefs about love were misguided. The movies explore similar themes of the challenges of modern dating, the fear of commitment, and the struggle to find lasting love.

One More Chance

One More Chance

3.6
2007

Both "One More Chance" and "(500) Days of Summer" follow the arc of a romantic relationship between two people that ultimately does not work out, despite the initial passion and connection. The male protagonist (Tom in (500) Days of Summer, Popoy in One More Chance) falls deeply in love and wants a committed relationship, while the female protagonist (Summer, Basha) is more hesitant about commitment and eventually breaks things off, leaving the male heartbroken. The movies explore the different perspectives on love, with the male believing in true love and the female being more pragmatic. There is a period of the male struggling to move on after the breakup, including attempts at dating others that fail. Eventually, both movies end with the exes meeting again after time apart, having grown and matured, leaving the possibility of rekindling their relationship open-ended. The overall themes of love, heartbreak, personal growth, and differing perspectives on relationships are central to both films' narratives. The story arcs follow a similar trajectory of a passionate relationship, breakup, the male's difficulty moving on, and a reunion after time apart and self-discovery.

Delicacy

Delicacy

3.2
2011

Both "Delicacy" and "(500) Days of Summer" follow a similar narrative arc of a romantic relationship that ultimately fails. The protagonists, Tom and Nathalie, fall for someone who is emotionally unavailable or unwilling to commit - Summer and Markus, respectively. Despite the initial passion and connection, the relationships deteriorate due to incompatibilities and differing expectations. Tom and Nathalie struggle to move on after the breakups, reflecting on the relationships and their own misconceptions. Eventually, they find closure and the possibility of new love, with Tom meeting Autumn and Nathalie embracing her future with Markus. The movies explore themes of love, heartbreak, self-discovery, and the complexities of modern relationships.

Drinking Buddies

Drinking Buddies

3.0
2013

Both "Drinking Buddies" and "(500) Days of Summer" explore the complexities of modern relationships and the challenges of navigating romantic feelings between friends. The central characters, Tom and Kate, develop deep connections with Summer and Luke respectively, but face uncertainty about the nature of their relationships due to differing expectations and commitment levels. The plots follow the ups and downs of these friendships turning into romantic entanglements, with moments of intimacy and passion contrasted by misunderstandings, jealousy, and heartbreak. Ultimately, the protagonists gain self-awareness and closure, realizing their idealized notions of love were misguided, and move forward with newfound perspectives on relationships and personal growth.

My Girlfriend's Boyfriend

My Girlfriend's Boyfriend

2.8
2010

Both "My Girlfriend's Boyfriend" and "(500) Days of Summer" center around a romantic relationship between the main characters that ultimately does not work out. In "(500) Days of Summer", Tom falls for Summer but she does not share his belief in true love, leading to their breakup. Similarly in "My Girlfriend's Boyfriend", Ethan falls deeply in love with Jesse but she struggles with revealing her inability to have children, fearing it will end their relationship. The movies explore the complexities of modern relationships, differing expectations, and the pain of heartbreak. They also follow the male protagonist's journey of self-discovery and growth after the relationship ends, as Tom rededicates himself to architecture and Ethan gets his novel published. The narratives are non-linear, using flashbacks and vignettes to depict the ups and downs of the relationships.

How to Be Single

How to Be Single

3.1
2016

Both "How to Be Single" and "(500) Days of Summer" follow the romantic lives and relationships of young adults navigating the complexities of modern dating and love. The central characters, Tom in "(500) Days of Summer" and Alice in "How to Be Single", experience the highs and lows of relationships that ultimately don't work out, forcing them to re-evaluate their perspectives on love and commitment. The movies explore themes of unrequited love, casual dating, and the search for "the one" through an ensemble cast of friends and love interests. The non-linear storytelling in "(500) Days of Summer" parallels the interweaving storylines in "How to Be Single" as the characters navigate different romantic situations. Both movies culminate with the protagonists embracing being single and open to new possibilities after their heartbreaks.

Love & Sex

Love & Sex

3.1
2000

Both "Love & Sex" and "(500) Days of Summer" follow the non-linear romantic relationships of the main characters, exploring the ups and downs of love, heartbreak, and finding the right partner. The protagonists, Tom and Kate, go through a series of failed relationships and misadventures before realizing their true feelings for their respective love interests, Summer and Adam. The movies depict the complexities of modern dating, the challenges of maintaining a relationship, and the importance of timing and compatibility in finding lasting love. They also highlight the personal growth and self-discovery that often accompanies the journey of finding the right partner.

Sidewalks of New York

Sidewalks of New York

3.1
2001

Both "(500) Days of Summer" and "Sidewalks of New York" explore the complexities of modern relationships and dating in an urban setting. The films follow a non-linear narrative structure, interweaving multiple storylines of characters navigating the ups and downs of romantic entanglements. The central themes revolve around the challenges of commitment, the disillusionment of idealized love, and the search for fulfillment and compatibility. The protagonists, Tom and Tommy, experience the highs of new relationships followed by the lows of breakups, forcing them to reevaluate their perspectives on love. The films offer a realistic portrayal of the emotional rollercoaster of dating, with characters grappling with issues of commitment, infidelity, and self-discovery. Ultimately, both movies underscore the complexities of human connections and the pursuit of finding lasting love in the modern urban landscape.

The Last Kiss

The Last Kiss

3.0
2006

Both "The Last Kiss" and "(500) Days of Summer" follow the story of a man in a committed relationship who becomes disillusioned and tempted by another woman, leading to infidelity that threatens to end the relationship. The main characters, Tom and Michael, initially seem happy with their partners Summer and Jenna but grow restless and question their commitment. They meet new women, Kim and Summer, who represent freedom and excitement. Despite their feelings for their partners, Tom and Michael cheat, devastating their girlfriends when the truth comes out. The movies explore themes of love, commitment, and the challenges of long-term relationships as the men grapple with their choices and attempt to reconcile with their partners or move on.

The Good Guy

The Good Guy

2.8
2009

Both "The Good Guy" and "(500) Days of Summer" follow a similar narrative arc of a romantic relationship that starts off promising but ultimately fails due to mismatched expectations and incompatibility between the two partners. In "(500) Days of Summer", Tom falls for Summer but she does not share his belief in true love, leading to their breakup. Similarly in "The Good Guy", Tommy's superficial relationship with Beth falls apart as she develops a deeper connection with Daniel. The movies parallel each other in depicting the male protagonist's idealized view of the relationship being challenged by the female partner's differing perspective. Tom and Tommy both struggle to accept that their relationships are not what they envisioned. The female characters, Summer and Beth, serve as catalysts that force the male leads to re-evaluate their notions of love and relationships. The stories also explore themes of disillusionment, growth, and moving on after a failed relationship. Both Tom and Tommy must come to terms with the end of their relationships and find new paths forward, with Tom rededicating himself to architecture and Tommy's fate left open-ended. The movies offer introspective character studies on the complexities of modern romance and the pitfalls of unrealistic expectations.

Celeste & Jesse Forever

Celeste & Jesse Forever

3.2
2012

Both "Celeste & Jesse Forever" and "(500) Days of Summer" follow the dissolution of a romantic relationship between two people who have different perspectives on love and commitment. In "(500) Days of Summer", Tom believes in true love while Summer is more casual about relationships, leading to their eventual breakup. Similarly in "Celeste & Jesse Forever", Celeste initiates a separation from Jesse despite his desire to reconcile, as she is not as invested in the marriage. The movies parallel each other in depicting the struggles of the characters to move on after the breakup. Tom and Celeste both have difficulty accepting the end of their relationships and continue to hold onto hope of reuniting with their former partners. They also experience periods of depression and attempts to distract themselves through work, hobbies, or dating others. Ultimately, both movies show the protagonists gaining closure and acceptance of the breakup. Tom realizes Summer was not "the one" for him, while Celeste comes to terms with her impulsive decision to divorce Jesse. They are able to wish their exes well and open themselves up to new possibilities for love in the future.

Last Christmas

Last Christmas

3.6
2019

Both "Last Christmas" and "(500) Days of Summer" follow a similar narrative arc of a romantic relationship that ultimately does not work out. The protagonists, Tom in (500) Days of Summer and Kate in Last Christmas, fall for someone who is emotionally unavailable or unable to fully commit. Despite their hopes and efforts, the relationships end, leaving the protagonists heartbroken and needing to re-evaluate their perspectives on love. However, by the end, they gain closure and a renewed outlook on life, with hints of potential new romantic interests. The movies explore themes of idealized love versus reality, personal growth through heartbreak, and finding purpose beyond romantic relationships. The stories parallel each other in their emotional journeys, character dynamics, and bittersweet yet hopeful conclusions.

Friends with Kids

Friends with Kids

3.0
2012

Both "Friends with Kids" and "(500) Days of Summer" explore the complexities of modern relationships and the challenges of finding lasting love. The central characters in each film - Tom and Summer in (500) Days of Summer, and Jason and Julie in Friends with Kids - begin as close friends who develop romantic feelings, though their perspectives on love and commitment differ. The films chronicle the ups and downs of their relationships, including periods of passion followed by disillusionment and heartbreak. A key similarity is the portrayal of the male protagonist initially idealizing the relationship, only to have his romantic notions shattered by the more pragmatic views of his female counterpart. Ultimately, both movies suggest that true love can emerge from friendship, but it requires mutual understanding and a willingness to overcome preconceived notions about relationships.