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Movies Like Why Not Both
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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.
Clueless
1995
Shallow, rich and socially successful Cher is at the top of her Beverly Hills high school's pecking scale. Seeing herself as a matchmaker, Cher first coaxes two teachers into dating each other. Emboldened by her success, she decides to give hopelessly klutzy new student Tai a makeover. When Tai becomes more popular than she is, Cher realizes that her disapproving ex-stepbrother was right about how misguided she was -- and falls for him.
The Choice
2016
Travis and Gabby first meet as neighbors in a small coastal town and wind up in a relationship that is tested by life's most defining events.
The Matchmaker's Playbook
2018
After a career-ending accident, former NFL recruit Ian Hunter is back on campus, and he's putting his extensive skills with women to work as one of the masterminds behind a successful and secretive dating service. But when Blake Olson requests the services of Wingmen, Inc., Ian may have landed his most hopeless client yet. As Blake begins the transformation from hot mess to smokin' hot, Ian realizes he's in danger of breaking his cardinal rule....
Emma.
2020
In 1800s England, a well-meaning but selfish young woman meddles in the love lives of her friends.
Endless Love
2014
A privileged girl and a charismatic boy's instant desire sparks a love affair made only more reckless by parents trying to keep them apart.
After Ever Happy
2022
As a shocking truth about a couple's families emerges, the two lovers discover they are not so different from each other. Tessa is no longer the sweet, simple, good girl she was when she met Hardin — any more than he is the cruel, moody boy she fell so hard for.
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?
My Sassy Girl
2008
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
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.
Marked Men: Rule + Shaw
2025
Shaw Landon has loved Rule Archer from the moment she laid eyes on him. Rule, a fiery-tempered rebel tattoo artist, doesn’t have time for a good girl pre-med student like Shaw — even if she’s the only one who can see the person he truly is. She lives by other people’s rules; he makes his own. But a short skirt, too many birthday cocktails, and spilled secrets lead to a night neither can forget. Now, Shaw and Rule must figure out how a girl like her and a guy like him are supposed to be together without destroying their love…or each other.
The Map That Leads to You
2025
Heather is a young woman traveling Europe with friends before starting her perfectly planned life. A chance meeting with Jack sparks an unexpected romance that leads to deep emotional discovery. As secrets and life choices test their bond, her path changes forever.
It Takes Two
1995
Identical 9-year-olds from very different backgrounds: orphaned Amanda and wealthy Alyssa meet at summer camp and decide to switch places -- and play matchmaker between Alyssa's dad, Roger, and the kind social worker who cares for Amanda.
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.
Brimming with Love
2018
Allie is an aspiring journalist who meets Sam, a coffee shop owner who plays matchmaker for his customers. Allie agrees to be matched but going though Sam's process causes her to see that her perfect match might just be the matchmaker himself.
Beyond the Sea
2004
Based on the life and career of legendary entertainer, Bobby Darin, the biopic moves back and forth between his childhood and adulthood, to tell the tale of his life.
How to Fall in Love
2012
An accountant, who never quite grew out of his awkward teenage years, finds himself with a dating coach - she happens to be his high school crush as well. Thanks to his coach, he gets a pretty woman he has his sights on for some time, but realizes they are incompatible. Meanwhile, his dating lessons with his teenage crush reawaken old feelings. Not realizing the feelings are mutual, he finds himself unable to act on them due to his fear of being rejected by the one he truly loves.
Crossing Delancey
1988
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.
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