Movies like Playing It Cool (2014)
The best movies like Playing It Cool (2014) are Someone Great (2019), ¿Quieres ser mi hijo? (2023) and Someone Like You... (2001). If Playing It Cool hooked you with its comedy and romance, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest rated¿Quieres ser mi hijo? (2023)8.4/10 from 378 votes
- NewestOne Night Only (2026)Released 2026
Someone Great (2019)
An aspiring music journalist lands her dream job and is about to move to San Francisco when her boyfriend of nine years decides to call it quits. To nurse her broken heart, she and her two best friends spend one outrageous last adventure in New York City.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like this¿Quieres ser mi hijo? (2023)
Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Absolute CinemaMovies 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 · both comedy & romance
Popcorn FlickMovies like thisThe List (2023)
After her fiance sleeps with a celebrity on his free pass list, Abby Meyers, with nothing but five names and a fantasy shared by millions, sets out for Los Angeles to sleep with someone from hers.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisPlayers (2024)
New York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it takes to go from simply scoring to playing for keeps.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisHow to Date Billy Walsh (2024)
Archie has been in love with his best friend Amelia for as long as he can remember. Just when he builds up the courage to declare his feelings, she falls head over heels for Billy Walsh, a new American transfer student.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisOne Night Only (2026)
Two love-starved strangers crash into each other on the one night of the year when single people are allowed to have sex.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Right Kind of Wrong (2013)
A stubborn idealist spies a bride on her way to her wedding and immediately falls in love with her.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisMy Sassy Girl (2008)
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe 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.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisZack and Miri Make a Porno (2008)
Lifelong platonic friends Zack and Miri look to solve their respective cash-flow problems by making an adult film together. As the cameras roll, however, the duo begin to sense that they may have more feelings for each other than they previously thought.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisDesperados (2020)
A panicked young woman and her two best friends fly to Mexico to delete a ranting email she sent to her new boyfriend. On arrival, they run into her former beau, who soon gets caught up in their frantic scheme.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisPicture This (2025)
Single and without a man on the horizon, Pia runs a failing photography studio in London with her best friend Jay. As her sister Sonal prepares for marriage and her mother Laxmi urges her to partner up, a spiritual guru predicts Pia will meet the love of her life among her next five dates. With her family intervening, Pia embarks on a hilarious yet heartfelt quest for love.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisI Want You Back (2022)
Peter and Emma thought they were on the precipice of life’s biggest moments – marriage, kids, and houses in the suburbs – until their respective partners dumped them. Horrified to learn that the loves of their lives have already moved on, Peter and Emma hatch a hilarious plan to win back their exes with unexpected results.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisSex Appeal (2022)
Avery, a teenager with a tendency towards perfectionism, enlists her friend Larson to help her prepare for her first time with her long-distance boyfriend.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisHow I Got Into College (1989)
High school senior Marlon Bowne is smitten with overachieving classmate Jessica Kailo. But, if he wants to have a shot with her, he'll have to find a way to get into Ramsey College, Jessica's top choice of schools. It won't be easy, since the college is highly selective and Marlon's grades are hardly impressive. That means the lovelorn teen will have to find a way to score high on the SATs and win over the college admissions committee.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisDinner in America (2022)
An on-the-lam punk rocker and a young woman obsessed with a local band go on an unexpected and epic journey together through the decaying suburbs of the American Midwest.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Worth the HypeMovies like thisAbout 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.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisSplendor (1999)
Veronica is a white-bread beauty searching for a good man in Los Angeles. While slam dancing at a Halloween rave, she meets Abel, a sensitive poet. Then she meets Zed, a supersexy tattooed drummer with incredible biceps. Who will she choose? Does she go for true love or cheap sex? She can't decide so she chooses both. But after managing to nurture a picture-perfect threesome, along comes Ernest, a rich movie director with deep baby blues that sweep Veronica off her feet. What's a girl to do now?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisFrench Girl (2024)
Sweet Gordon, an affable English teacher in Brooklyn, has beaten the odds; a French Girl has fallen in love with him and he’s fallen even harder back. But their future is thrown into limbo when she interviews for an executive chef position in her hometown of Quebec City. To Gordon’s dismay her future boss also happens to be her former lover, a celebrity Chef with oceanic eyes and a hit TV show. Good luck Gordon.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisA French Pursuit (TBA)
Zoe Turner, an unconventional and lively British art teacher, falls head over heels for fellow rebel spirit Jean-Louis. But when their plans for a romantic getaway are dashed, she’s heartbroken. Zoe thus embarks on a daring pursuit of Jean-Louis in the picturesque Cévennes deep in the South of France. Accompanied by the determined donkey Napoleon, Zoe grapples with the absurdities and challenges of their journey. Along the way, they encounter new friends and perils that draw them closer, prompting Zoe to reevaluate her priorities, confront her life choices, and rediscover her joie de vivre.
Why it matches: Similar story and style · both comedy & romance
Green Card (1990)
Urban horticulturalist Brontë Mitchell has her eye on a gorgeous apartment, but the building's board will rent it only to a married couple. Georges Fauré, a waiter from France whose visa is expiring, needs to marry an American woman to stay in the country. Their marriage of convenience turns into a burden when they must live together to allay the suspicions of the immigration service, as the polar opposites grate on each other's nerves.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisTo All the Boys I've Loved Before (2018)
Lara Jean's love life goes from imaginary to out of control when her secret letters to every boy she's ever fallen for are mysteriously mailed out.
Why it matches: Similar story and style · both comedy & romance
Worth the HypeMovies like thisWe Love You, Sally Carmichael! (2017)
Readers across the world are in love with author Sally Carmichael's series of romance novels that chronicle the epic love story between a human girl and a merman. But no one knows that Sally Carmichael is really Simon Hayes, a bitter, serious novelist - and Simon would like to keep it that way. When he is forced to meet a movie star about the movie adaptation, his life of anonymity starts to crumble.
Why it matches: Similar story and style · both romance & comedy
Kadhal Desam (1996)
Two boys from rival colleges, one rich and the other poor, become good friends after an incident. A new girl in college makes both their hearts melt but neither realises that they love the same girl.
Why it matches: Similar story and style · both comedy & romance
My secretary is mad... mad... mad... (1967)
The aviation company for which Ricardo works gives a secretary a trip to Peru.
Why it matches: Similar story and style · both comedy & romance
Heaven Can Wait (1978)
Joe Pendleton is a quarterback preparing to lead his team to the superbowl when he is almost killed in an accident. An overanxious angel plucks him to heaven only to discover that he wasn't ready to die, and that his body has been cremated. A new body must be found, and that of a recently-murdered millionaire is chosen. His wife and accountant—the murderers—are confused by this development, as he buys the L.A. Rams in order to once again quarterback them into the Superbowl.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisFour Christmases (2008)
Brad and Kate have made something of an art form out of avoiding their families during the holidays, but this year their foolproof plan is about go bust -- big time. Stuck at the city airport after all departing flights are canceled, the couple is embarrassed to see their ruse exposed to the world by an overzealous television reporter. Now, Brad and Kate are left with precious little choice other than to swallow their pride and suffer the rounds.
Why it matches: Similar story and style · both comedy & romance
SnoozefestMovies like thisWould You Still Love Me? (2023)
A romantic picnic takes an unexpected turn.
Why it matches: Similar story and style · both romance
Joe's Apartment (1996)
A nice guy has just moved to New York and discovers that he must share his run-down apartment with a couple thousand singing, dancing cockroaches.
Why it matches: Similar story and style · both comedy
SnoozefestMovies like this
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Frequently asked questions
What are the best movies like Playing It Cool?
The closest matches to Playing It Cool are Someone Great (2019), ¿Quieres ser mi hijo? (2023) and Someone Like You... (2001). Below are 27 more, each with the reason it matches.
What should I watch after Playing It Cool?
Start with Someone Great (2019), the closest match to Playing It Cool.
What is the highest-rated movie like Playing It Cool?
¿Quieres ser mi hijo? (2023), rated 8.4/10 by 378 TMDB users.
What is the newest movie like Playing It Cool?
One Night Only (2026) is the most recent release on this list.
Are there English movies like Playing It Cool?
Yes: Someone Great (2019), ¿Quieres ser mi hijo? (2023) and Someone Like You... (2001).
How are movies similar to Playing It Cool chosen?
First come films that Trakt’s viewers watch alongside Playing It Cool, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.