Secret Admirer
An anonymous love letter left in Michael Ryan's locker on the last day of school wreaks havoc on his life and the lives of everyone who comes in contact with it.…
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Movies Like Playing It Cool
If you liked Playing It Cool, this Cinento mix gives you more titles with a similar feeling, rhythm, tension, comfort level, and after-watch taste. Start with 16 picks, then load more when you want a wider path.
Movies Like Playing It Cool
A Touch of Class
Steve, a happily married American man living in London meets Vicki, an English divorcée and run off to Marbella for a rollicking week of sex. They then return to London to set up a…
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My Fake Boyfriend
A young man in a tricky situation follows the advice of his unconventional best friend and uses social media to create a fake boyfriend to keep his awful ex-lover out of his life. …
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No Hard Feelings
On the brink of losing her childhood home, Maddie discovers an intriguing job listing: wealthy helicopter parents looking for someone to “date” their introverted 19-year-old son, P…
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Girl on a Bicycle
Paolo, an Italian tour bus driver living in Paris, has just summoned up the courage to propose marriage to his German girlfriend Greta. However, a chance encounter with a French wo…
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Bye Bye Love
With varying degrees of success, recently divorced friends Dave, Vic and Donny are trying to move on with their lives. Vic feels vilified by his ex-wife's parents, while Donny has …
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A Nice Girl Like You
Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her…
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Bros
Two gay men are possibly, probably, stumbling towards love. Maybe. They're both very busy.…
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Teacher's Pet
A rugged city editor poses as a journalism student and flirts with the professor.…
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Cuban Fury
Beneath Bruce Garrett's under-confident, overweight exterior, the passionate heart of a salsa king lies dormant. Now, one woman is about to reignite his Latin fire.…
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Puppy Love
After a disastrous first date, wild-child Nicole and socially-anxious Max vow to lose each other’s numbers until they learn that their dogs found a love match, and now puppies are …
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The Ugly Truth
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 an…
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Starting Over
After divorcing his ambitious singer wife, a middle-aged man begins a new relationship with a teacher.…
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We Broke Up
Lori and Doug break up right before Lori's sister's wedding and decide to pretend they're still together for the weekend as to not disrupt the fun.…
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The Knack... and How to Get It
A nebbish schoolteacher begs his smooth (and misogynistic) pal to teach him 'the knack' – how to score with women. Serendipitously, the men meet up with a new girl in town, as well…
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That Awkward Moment
Best pals Jason and Daniel indulge in casual flings and revel in their carefree, unattached lives. After learning that the marriage of their friend Mikey is over, they gladly welco…
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The Dog Problem
In the film, Solo is a down-on-his-luck writer who is encouraged by his psychiatrist to get a dog. Solo meets his love interest, who he assumes to be a dog owner when meeting her a…
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How to Be Single
New York City is full of lonely hearts seeking the right match, and what Alice, Robin, Lucy, Meg, Tom and David all have in common is the need to learn how to be single in a world …
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Long Weekend
Bart's chance encounter with the enigmatic Vienna leads to a whirlwind weekend together. The two fall fast and hard, but both carry secrets that could be their undoing or the chanc…
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A Guy Thing
Paul Morse is a good guy. When his friends throw him a wild bachelor party, he just wants to keep his conscience clean -- which is why he's shocked when he wakes up in bed with a b…
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The Seven Year Itch
When his family goes away for summer vacation, a hitherto faithful publishing executive with an overactive imagination is tempted by an attractive new neighbor.…
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The 4:30 Movie
In the summer of 1986, three sixteen year old friends spend their Saturdays sneaking into movies at the local multiplex. But when one of the guys also invites the girl of his dream…
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American Pie 2
After a year apart - attending different schools, meeting different people - the guys rent a beach house and vow to make this the best summer ever. As it turns out, whether that wi…
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Maintenance Required
Charlie, the fiercely independent owner of an all-female mechanic shop, is forced to reevaluate her future when a flashy corporate competitor moves in across the street. Seeking co…
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The Tao of Steve
In college, Dex was the big man on campus. Ten years later, now an overweight kindergarten teacher, Dex is immune to the shocked stares of the women who were once his conquests. Wh…
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The 40 Year Old Virgin
Andy Stitzer has a pleasant life with a nice apartment and a job stamping invoices at an electronics store. But at age 40, there's one thing Andy hasn't done, and it's really bothe…
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The Last Summer
Standing on the precipice of adulthood, a group of friends navigate new relationships, while reexamining others, during their final summer before college.…
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Valley Girl
Julie, a girl from the valley, meets Randy, a punk from the city. They are from different worlds and find love. Somehow they need to stay together in spite of her trendy, shallow f…
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Romance & Cigarettes
Ironworker Nick lives with his wife, Kitty, and three daughters. When he meets a significantly younger woman, Tula, he starts an affair with her, much to the chagrin of his wife, a…
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The Wrong Missy
A guy meets the woman of his dreams and invites her to his company's corporate retreat, but realizes he sent the invite to the wrong person.…
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At Midnight
Alejandro's life is disrupted when actress Sophie Wilder stays at his hotel. To their surprise, the two fall for one another, meeting at midnight.…
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Dinner in America
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.…
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Standby
Twenty-something Alan (Gleeson) is down on his luck. Stood up at the altar and recently fired from his banking job, he finds himself working with his mother as a part-time tourist …
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Attraction
A writer/radio advice show host fails to heed his own advice as he stalks his ex-girlfriend and then becomes involved with an actress friend of hers.…
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The Answer Man
Twenty years ago, Arlen Faber wrote a book about spirituality that became wildly popular. These days, he's a curmudgeonly recluse who only enjoys the company of his chiropractor, E…
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The Wedding Year
A commitment-phobic 27-year old’s relationship is put to the test when she and her boyfriend attend 7 weddings in the same year.…
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Love Potion No. 9
Unlucky in love, chemist Paul Matthews visits gypsy Madame Rosa for help. Quickly realizing he is a hopeless nerd, she gifts him with Love Potion No. 8, which makes anyone who wear…
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Friends with Benefits
Dylan is done with relationships. Jamie decides to stop buying into the Hollywood clichés of true love. When the two become friends they decide to try something new and take advant…
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Zack and Miri Make a Porno
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 tha…
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The Perfect Find
After a high-profile firing, everything is at stake for 40-year-old Jenna: her career, her ticking biological clock, and her bank account. Her fashion career comeback hits a snag w…
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How should I use Movies Like Playing It Cool?
Start with the first row of picks and choose the title that matches your mood tonight. Use Load More when you want a wider path without leaving the same feeling zone.
Why do these picks belong together?
Cinento looks at the feeling behind the search: tone, pacing, tension, comfort level, genre lane, and the kind of emotional aftertaste people usually want from this mix.
Is this mix only for people who already know the main title?
No. The title is a shortcut. You can use the mix even if you simply want the same mood, pressure, or story energy.
Can I find official watch options from here?
Yes. Open any title card and check the Stream / Rent / Buy section for official provider options when they are available in your region.