(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.
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.
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.
People We Meet on Vacation
2026★ 6.9
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.
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.
Another Year
2010★ 7.0
During a year, a very content couple approaching retirement are visited by friends and family less happy with their lives.
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.
Singles
1992★ 6.4
A group of young adults in their twenties, who share an apartment in the city of Seattle, ponder on love and face all the challenges of adulthood.
Sidewalks of New York
2001★ 6.0
The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives, the film weaves a humorous and biting commentary on the game of love -- easy to start, hard to finish.
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.
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.
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.
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.
Spoiler Alert
2022★ 7.0
Journalist Michael Ausiello embarks on a rollercoaster ride of emotions when Kit Cowan, his partner of 14 years, is diagnosed with terminal cancer.
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?
Danny Deckchair
2003★ 6.1
An unappreciated laborer's patience reaches breaking point when his girlfriend cancels a romantic holiday. Making light of the situation, he decides to tie hundreds of helium balloons to a chair in an outlandish bid to float to a new life.
Crossing Delancey
1988★ 5.9
Thirty-something Isabelle spends her time going from her tiny, solitary West Side apartment to that of her grandmother on the Lower East Side. While her grandmother plots to find her a romantic match, Isabelle is courted by a married, worldly author, Anton, yet can't seem to shake the down-to-earth appeal of Sam, a pickle vendor.
Waiting for Forever
2010★ 5.9
A Hollywood-set romantic tale of a guy who is content to live his life without a job yet with the love of his life, a young actress.