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Movies Like The 17 Greatest Dates of Matthew Reading
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Crazy, Stupid, Love.
Community rank #306 · 2011
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.
Play It Again, Sam
1972
A neurotic film critic obsessed with the movie Casablanca attempts to get over his wife leaving him by dating again with the help of a married couple and his illusory idol, Humphrey Bogart.
One Day
2011
A romantic comedy centered on Dexter and Emma, who first meet during their graduation in 1988 and proceed to keep in touch regularly. The film follows what they do on July 15 annually, usually doing something together.
Whatever Works
2009
Whatever Works explores the relationship between a crotchety misanthrope, Boris and a naïve, impressionable young runaway from the south, Melody. When Melody's uptight parents arrive in New York to rescue her, they are quickly drawn into wildly unexpected romantic entanglements. Everyone discovers that finding love is just a combination of lucky chance and appreciating the value of "whatever works."
Fresh
2022
Frustrated by scrolling dating apps only to end up on lame, tedious dates, Noa takes a chance by giving her number to the awkwardly charming Steve after a produce-section meet-cute at the grocery store.
Set It Up
2018
Two overworked and underpaid assistants come up with a plan to get their bosses off their backs by setting them up with each other.
How to Lose a Guy in 10 Days
2003
It's the battle of wills, as Andie needs to prove she can dump a guy in 10 days, whereas Ben needs to prove he can win a girl in 10 days. Now, the clock is ticking—and the wildly entertaining comedy smash is off and running in this irresistible tale of sex, lies and outrageous romantic fireworks!
Carrie Pilby
2017
Awkward, isolated and disapproving of most of the people around her, a precocious 19-year-old genius is challenged to put her convictions to the test by venturing out on to the NYC dating scene.
Chasing Papi
2003
Playboy Thomas Fuentes has so far been able to skate by in life on good looks and charm alone. But when his duplicitous relationships with three women -- impassioned waitress Cici, meticulous lawyer Lorena and bored socialite Patricia -- spiral out of control, he suffers a mental breakdown. His doctor recommends that he choose just one girlfriend -- but can he choose in time before they discover his deception?
The Wrong Paris
2025
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.
Hitch
2005
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.
What's Your Number?
2011
Ally Darling is realizing she's a little lost in life. Her latest romance has just fizzled out, and she's just been fired from her marketing job. Then she reads an eye-opening magazine article that warns that 96 percent of women who've been with 20 or more lovers are unlikely to find a husband. Determined to turn her life around and prove the article wrong, Ally embarks on a mission to find the perfect mate from among her numerous ex-boyfriends.
Love, Guaranteed
2020
A lawyer takes on a new client that wants to sue a dating website because it guarantees love.
How to Be Single
2016
New York City is full of lonely hearts seeking the right match, and what Alice, Robin, Lucy, Meg, Tom and David all have in common is the need to learn how to be single in a world filled with ever-evolving definitions of love.
The Incredible Jessica James
2017
Burned by a bad breakup, a struggling New York City playwright makes an unlikely connection with a divorced app designer she meets on a blind date.
Kissing Jessica Stein
2002
Jessica, a Jewish copy editor living and working in New York City, is plagued by failed blind dates with men, and decides to answer a newspaper's personal advertisement. The advertisement has been placed by 'lesbian-curious' Helen Cooper, a thirtysomething art gallerist.
About Last Night
2014
Bernie and Joan are two fiery flirters who are passionate about everything from hookups to breakups and each other. When he sets up his best friend, Danny, with her roommate, Debbie, the sparks soon fly as they try to navigate the relationship minefields from the bar to the bedroom and are eventually put to the test in the real world.
Bye Bye Love
1995
With varying degrees of success, recently divorced friends Dave, Vic and Donny are trying to move on with their lives. Vic feels vilified by his ex-wife's parents, while Donny has a shaky bond with his teen daughter, Emma. Dave, meanwhile, has an enviable problem -- he has more dates than he can handle. As they confront their post-marital challenges, the men take solace in one another's plights.
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