(500) Days of Summer
Tom, greeting-card writer and hopeless romantic, is caught completely off-guard when his girlfriend, Summer, suddenly dumps him. He reflects on their 500 days together to try to figure out where their love affair went sour, and in doing so, Tom rediscovers his true passions in life.
Movies Like (500) Days of Summer
Similar in style, tone, and themes — find your next watch.
Catch and Release
2006★ 5.9
For a grieving fiancée, learning to love again requires the help of her late love's three best friends.
Hitch
2005★ 6.6
Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques fail to work on Sara Melas, a tabloid reporter digging for dirt on Allegra Cole's love life. When Sara discovers Hitch's connection to Albert – now Allegra's boyfriend – it threatens to destroy both relationships.
One Day
2011★ 7.4
After spending the night together on the eve of their college graduation, Dexter and Emma are shown each year on the same date to see where they are in their lives. They are sometimes together, and sometimes not.
The Wrong Paris
2025★ 6.7
Dawn thinks she's joining a dating show in Paris, France, only to land in Paris, Texas. She has an exit plan — until sparks fly with the cowboy bachelor.
Young Adult
2011★ 5.8
A divorced writer from the Midwest returns to her hometown to reconnect with an old flame, who's now married with a family.
Yoh! Bestie
2026★ 6.2
Thando is perpetually unlucky in love, but when her bestie returns from his travels with a fiancée in tow, she's forced to face a new emotion — jealousy.
Café Society
2016★ 6.4
The story of a young man who arrives in Hollywood during the 1930s hoping to work in the film industry, falls in love, and finds himself swept up in the vibrant café society that defined the spirit of the age.
Irreplaceable You
2018★ 6.9
A stunning cancer diagnosis spurs Abbie to seek a future girlfriend for fiancé and childhood sweetheart Sam, who's clueless when it comes to dating.
The Private Lives of Pippa Lee
2009★ 5.8
After her much older husband forces a move to a suburban retirement community, Pippa Lee engages in a period of reflection and finds herself heading toward a quiet nervous breakdown.
Which Brings Me to You
2023★ 6.2
Two romantic burnouts, Jane and Will, are immediately drawn to each other at a mutual friend’s wedding. After a disastrous hookup in the coatroom, the two spend the next 24 hours together, trading candid confessions of messy histories and heartbreak, on the off chance that this fling might be the real thing.
New York, I Love You
2008★ 6.0
New York, I Love You delves into the intimate lives of New Yorkers as they grapple with, delight in and search for love. Journey from the Diamond District in the heart of Manhattan, through Chinatown and the Upper East Side, towards the Village, into Tribeca, and Brooklyn as lovers of all ages try to find romance in the Big Apple.
Crazy, Stupid, Love.
2011★ 7.3
Cal Weaver is living the American dream. He has a good job, a beautiful house, great children and a beautiful wife, named Emily. Cal's seemingly perfect life unravels, however, when he learns that Emily has been unfaithful and wants a divorce. Over 40 and suddenly single, Cal is adrift in the fickle world of dating. Enter, Jacob Palmer, a self-styled player who takes Cal under his wing and teaches him how to be a hit with the ladies.
Is This Thing On?
2025★ 6.6
As their marriage quietly unravels, Alex faces middle age and an impending divorce, seeking new purpose in the New York comedy scene while Tess confronts the sacrifices she made for their family—forcing them to navigate co-parenting, identity, and whether love can take a new form.
People We Meet on Vacation
2026★ 7.0
Poppy's a free spirit. Alex loves a plan. After years of summer vacations, these polar-opposite pals wonder if they could be a perfect romantic match.
A Lot Like Love
2005★ 6.8
On a flight from Los Angeles to New York, Oliver and Emily make a connection, only to decide that they are poorly suited to be together. Over the next seven years, however, they are reunited time and time again, they go from being acquaintances to close friends to... lovers?
Licorice Pizza
2021★ 6.9
The story of Gary Valentine and Alana Kane growing up, running around and going through the treacherous navigation of first love in the San Fernando Valley, 1973.
Home Again
2017★ 6.1
Life for a single mom in Los Angeles takes an unexpected turn when she allows three young guys to move in with her.
My Girl
1991★ 7.4
Vada Sultenfuss is obsessed with death. Her mother is dead, and her father runs a funeral parlor. She is also in love with her English teacher, and joins a poetry class over the summer just to impress him. Thomas J., her best friend, is "allergic to everything", and sticks with Vada despite her hangups. When Vada's father hires Shelly, and begins to fall for her, things take a turn to the worse...
Bridget Jones: Mad About the Boy
2025★ 6.4
Bridget Jones navigates life as a widow and single mum with the help of her family, friends, and former lover, Daniel. Back to work and on the apps, she's pursued by a younger man and maybe – just maybe – her son's science teacher.
Say Anything...
1989★ 7.0
Average student and eternal optimist Lloyd Dobler seeks to capture the heart of Diane Court, a beautiful but unattainable valedictorian classmate. He surprises just about everyone - including himself - when she returns the sentiment. However, Diane's divorced, over-protective father soon begins to disapprove of the match, and Lloyd realises that it's going to take more than just the power of love to conquer all.