Movies Like CheckMating

If you liked CheckMating (1996), a movie directed by William Azaroff, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Anything for Love (2016)
★ 6/10
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.
2
The Wrong Paris (2025)
★ 6.7/10
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.
3
The Ugly Truth (2009)
★ 6.5/10
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…
4
The Love Hypothesis (2026)
★ 7.9/10
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.
5
Love by Chance (2016)
★ 5.9/10
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…
6
Hitch (2005)
★ 6.6/10
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…
7
Clueless (1995)
★ 7.2/10
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…
8
Only You (1994)
★ 6.7/10
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…
9
Royal Matchmaker (2018)
★ 6.7/10
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…
10
Lady Chatterley's Lover (2022)
★ 6.7/10
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.
11
Set It Up (2018)
★ 6.9/10
Two overworked and underpaid assistants come up with a plan to get their bosses off their backs by setting them up with each other.
12
Mr. Jealousy (1998)
★ 5.9/10
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…
13
Crossing Delancey (1988)
★ 5.9/10
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…
14
Play It Again, Sam (1972)
★ 7.5/10
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.
15
Someone Like You... (2001)
★ 6/10
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…
16
Emma. (2020)
★ 7/10
In 1800s England, a well-meaning but selfish young woman meddles in the love lives of her friends.
17
Sleuth (1972)
★ 7.7/10
A man who loves games and theatre invites his wife's lover to meet, setting up a battle of wits with potentially deadly results.
18
Duplicity (2009)
★ 5.9/10
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…
19
How to Lose a Guy in 10 Days (2003)
★ 6.9/10
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…
20
What's Your Number? (2011)
★ 6.5/10
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…