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Movies Like CheckMating
Find movies like CheckMating using TMDB similarity plus Movie Rankings community context. Our top current pick is Crazy, Stupid, Love.. Browse 18 related titles with direct links to rankings, cast pages, and matchup data.
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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.
Sleuth
1972
A man who loves games and theatre invites his wife's lover to meet, setting up a battle of wits with potentially deadly results.
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.
Emma.
2020
In 1800s England, a well-meaning but selfish young woman meddles in the love lives of her friends.
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.
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.
Only You
1994
Two childhood paranormal incidents have convinced schoolteacher Faith Corvatch that her true love is a guy named 'Damon Bradley', but she has yet to meet him. Preparing to marry podiatrist Dwayne in ten days, Faith receives a phone call from Dwayne's old classmate Damon Bradley, who is on his way to Venice. She impulsively decides to fly to Italy with the hope of finally encountering the man of her dreams. Accompanying her on the trip is her sister-in-law and best friend Kate, who has just left her husband, Faith's brother Larry.
Lady Chatterley's Lover
2022
After a crippling injury leaves her husband impotent, Lady Chatterly is torn between her love for her husband and her physical desires. With her husband's consent, she seeks out other means of fulfilling her needs.
Royal Matchmaker
2018
A struggling NYC matchmaker is hired by a king to find his son a suitable wife in time for a national celebration. As the clock ticks towards her deadline, the matchmaker finds him the perfect wife -- only to realize that she’s fallen in love with him!
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.
The Ugly Truth
2009
A romantically challenged morning show producer is reluctantly embroiled in a series of outrageous tests by her chauvinistic correspondent to prove his theories on relationships and help her find love. His clever ploys, however, lead to an unexpected result.
Cooking with Love
2018
Optimistic and cheerful TV producer, Kelly, doesn’t have time for love. Bad boy celebrity chef, Stephen, doesn’t have time for anything besides cooking. Fun with a side of love ensues as Kelly and Stephen are paired on a children's cooking show.
Anything for Love
2016
Katherine, a high-powered executive who believes men are intimidated by her career, is persuaded by her friend to create an internet dating profile claiming she is an executive assistant.
Love by Chance
2016
Claire, an ambitious pastry chef, is busy running her new restaurant, but her meddling mom is preoccupied with her lack of love life. Without her knowledge, Claire’s mother finds her the perfect man, but when Claire finds out it wasn’t fate that brought them together, it could ruin the relationship.
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.
Someone Like You...
2001
Jane Goodale has everything going for her. She's a producer on a popular daytime talk show, and is in a hot romance with the show's dashing executive producer Ray. But when the relationship goes terribly awry, Jane begins an extensive study of the male animal, including her womanizing roommate Eddie. Jane puts her studies and romantic misadventure to use as a pseudonymous sex columnist -- and becomes a sensation.
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