Movies like CheckMating (1996)
The best movies like CheckMating (1996) are Love by Chance (2016), The Wrong Paris (2025) and The Ugly Truth (2009). If CheckMating hooked you, these 20 similar films are what to watch next, and every pick says why it matches.
CheckMating
Quick picks
- Highest ratedThe Love Hypothesis (2026)7.9/10 from 727 votes
- NewestThe Love Hypothesis (2026)Released 2026
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.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisThe 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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe 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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisThe Love Hypothesis (2026)
Olive Smith, a biology PhD candidate, and Dr. Adam Carlsen, a hotshot professor and well-known tyrant, enter into a fake relationship, seeing each of their carefully calculated theories on love get thrown into chaos.
Why it matches: Recommended by TMDB viewers
Absolute CinemaMovies like thisHitch (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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisAnything 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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisClueless (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.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisOnly 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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisLady 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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisSet 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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisCrossing 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.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisMr. Jealousy (1998)
After his first date at age 15 ended with the girl making out with another man at a party, aspiring writer Lester Grimm has treated all his girlfriends with jealousy and suspicion. While dating Ramona Ray, paranoia gets the best of him when he discovers that her most recent ex is successful novelist Dashiell Frank. Lester begins attending the same group therapy sessions as Dashiell to learn about Ramona's past with him.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisPlay 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.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisRoyal 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!
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisLove Under the Stars (2015)
Young at heart graduate student Becca strikes up an unlikely friendship with Emily, a quiet girl who recently lost her mother. With every passing play date chaperoned by Emily's father, Becca helps Emily come out of her shell and cope with her loss, and Emily teaches Becca to take on adult responsibilities. When a romance develops between Becca and Nate, though, the two must learn to balance their new relationship with Nate's responsibility to Emily, and with Becca's responsibility to finish her education.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisSomeone 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.
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like thisEmma. (2020)
In 1800s England, a well-meaning but selfish young woman meddles in the love lives of her friends.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisDuplicity (2009)
Two romantically involved government operatives Claire Stenwick and Ray Koval team up to manipulate a race between opposing corporations to corner the market on a medical innovation that will reap huge profits and allow them to lead an extravagant lifestyle together. They find themselves on opposing sides as corporate spies; however, as they each try to outdo the other, neither one can decide how far to trust the other in this high-stakes game of cat-and-mouse.
Why it matches: Recommended by TMDB viewers
SnoozefestMovies like thisSleuth (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.
Why it matches: Recommended by TMDB viewers
Worth the HypeMovies like thisHow 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!
Why it matches: Recommended by TMDB viewers
Popcorn FlickMovies like this
Like CheckMating and something else?
Blend two favourites and we’ll find the films in between.
Frequently asked questions
What are the best movies like CheckMating?
The closest matches to CheckMating are Love by Chance (2016), The Wrong Paris (2025) and The Ugly Truth (2009). Below are 17 more, each with the reason it matches.
What should I watch after CheckMating?
Start with Love by Chance (2016), the closest match to CheckMating.
What is the highest-rated movie like CheckMating?
The Love Hypothesis (2026), rated 7.9/10 by 727 TMDB users.
What is the newest movie like CheckMating?
The Love Hypothesis (2026) is the most recent release on this list.
How are movies similar to CheckMating chosen?
First come films that Trakt’s viewers watch alongside CheckMating, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.