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Movies like Playing It Cool

Key Features:
Romantic comedy, Unrequited love, Manic Pixie Dream Girl, Unconventional narrative, Fantasy elements, Non-linear narrative, Quirky, Love at first sight, Relationship challenges, Self-discovery
Tone:
whimsical, humorous, stylized
Target Audience:
Rom-com fans, Quirky romance lovers, Stylized narratives, Fantasy elements
Emotional Arc:
Infatuation → Acceptance

Playing It Cool

2014-09-26
Playing It Cool Poster - Find Similar Movies

A young man meets and instantly falls in love with an engaged woman.

Genres
Comedy, Romance
Cast
Chris Evans, Michelle Monaghan, Topher Grace, Aubrey Plaza, Luke Wilson, Martin Starr, Anthony Mackie, Ioan Gruffudd, Philip Baker Hall, Patrick Warburton
Crew
Justin Reardon, Chris Shafer, Paul Vicknair
Rating
5.844(790 votes)
Playing It CoolPlaying It Cool
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When We First Met
6.56

Using a magical photo booth that sends him back in time, Noah relives the night he met Avery over and over, trying to persuade her to fall for him.



Young Adult
5.8

A divorced writer from the Midwest returns to her hometown to reconnect with an old flame, who's now married with a family.



Just Friends
6.218

While visiting his hometown during Christmas, a man comes face-to-face with his old high school crush whom he was best friends with – a woman whose rejection of him turned him into a ferocious womanizer.



Boys and Girls
5.943

Ryan and Jennifer are opposites who definitely do not attract. At least that's what they always believed. When they met as twelve-year-olds, they disliked one another. When they met again as teenagers, they loathed each other. But when they meet in college, the uptight Ryan and the free-spirited Jennifer find that their differences bind them together and a rare friendship develops.



Prelude to a Kiss
5.613

A couple fall in love despite the girl's pessimistic outlook. As they struggle to come to terms with their relationship, something supernatural happens that tests it.



Safety Not Guaranteed
6.777

Three magazine employees head out on an assignment to interview a guy who placed a classified ad seeking a companion for time travel.



L.A. Story
6.489

With the help of a talking freeway billboard, a "wacky weatherman" tries to win the heart of an English newspaper reporter, who is struggling to make sense of the strange world of early-90s Los Angeles.



Crazy, Stupid, Love.

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.



Starstruck
7

Pop star Christopher Wilde has fame, fortune and a big-budget Hollywood movie awaiting him. But after meeting Jessica Olson, a down-to-earth girl from the Midwest, he is faced with following his heart or doing what's best for his career.



#realityhigh
6.257

When nerdy high schooler Dani finally attracts the interest of her longtime crush, she lands in the cross hairs of his ex, a social media celebrity.



Playing by Heart
6.579

In a vibrant tapestry of love and longing, nine interconnected souls navigate romance and heartbreak in L.A., where passions collide and truths unfold, revealing that the heart's desires often lead us where we least expect.



The First Time
6.99

A spark of attraction smolders, then ignites, between two teens from different high schools who meet by chance at a party.



Meet Cute
Meet Cute(2022)
5.834

A wildly inventive deconstruction of the romantic comedy built around the question: What would you do if you could travel to your loved ones’ past, heal their traumas, fix their problems, and change them into the perfect partner?



The Incredibly True Adventure of Two Girls in Love

An adventurous love story between two young women of different social and economic backgrounds who find themselves going through all the typical struggles of a new romance.



He's Just Not That Into You

Have you ever sat by the phone wondering why he said he would call, but didn't, or you can't figure out why she doesn't want to sleep with you anymore, or why your relationship just isn't going to the next level... they're just not that into you. Gigi just wants a man who says he'll call—and does—while Alex advises her to stop waiting by the phone. Beth wants a proposal after years of a committed relationship with her boyfriend, Neil, who sees nothing wrong with the status quo. Janine's not sure if she can trust her husband, Ben, who can't quite trust himself around Anna. Anna can't decide between the sexy married guy, or her straightforward, no-sparks standby, Conor, who can't get over the fact that he can't have her. And Mary, who's found an entire network of loving, supportive men, just needs to find one who's straight.



Isn't It Romantic
6.2

For a long time, Natalie, an Australian architect living in New York City, had always believed that what she had seen in rom-coms is all fantasy. But after thwarting a mugger at a subway station only to be knocked out while fleeing, Natalie wakes up and discovers that her life has suddenly become her worst nightmare—a romantic comedy—and she is the leading lady.



Flirting
Flirting(1991)
6.7

Two freethinking teenagers - a boy and a girl - confront with authoritarian teachers in their boarding schools. The other students treat this differently.



Virtual Sexuality
5.151

A frustrated teenage girl creates her perfect man in a virtual reality machine and in a freak accident, gives him life.



Sex Appeal
6.637

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.



IF
IF(2024)
7

After discovering she can see everyone's imaginary friends, a girl embarks on a magical adventure to reconnect forgotten imaginary friends with their kids.



Playing Doctor
5.892

Andi has had an inferiority complex since childhood and not only has to deal with it, but also with girls, feelings and genitalia in different sizes.



Bliss
Bliss(2021)
5.498

A mind-bending love story following Greg who, after recently being divorced and then fired, meets the mysterious Isabel, a woman living on the streets and convinced that the polluted, broken world around them is just a computer simulation. Doubtful at first, Greg eventually discovers there may be some truth to Isabel’s wild conspiracy.



Almost Friends
6.3

A man in his mid-20s, still living at home with his mother and stepfather, puts all his eggs in one basket: the girl who works at his local coffee shop. The problem is, she has a serious boyfriend. As they become closer, the line between friendship and intimacy is blurred, and the situation forces both to examine where they are in their lives.



Non-Transferable
5.6

Amy Tyler has planned the perfect surprise vacation for her boyfriend Josh Merit. But the real surprise is on her when he breaks things off on their anniversary. Stuck with reservations in her ex-boyfriend's name, Amy's two best friends suggest if Amy can't change the tickets ... why not change the guy?



Good on Paper
5.6

After years of putting her career ahead of love, stand-up comic Andrea Singer has stumbled upon the perfect guy. On paper, he checks all the boxes, but is he everything he appears to be?



Stargirl
Stargirl(2020)
7.4

An unassuming high schooler finds himself inexplicably drawn to the free-spirited new girl, whose unconventional ways change how they see themselves…and their world.



That's Not Cheating
5.802

Mateo and Camila, a couple that allow each other being unfaithful with a unreachable someone chosen by each.



Love Hard
Love Hard(2021)
6.928

An LA girl, unlucky in love, falls for an East Coast guy on a dating app and decides to surprise him for Christmas, only to discover that she's been catfished. But the object of her affection actually lives in the same town, and the guy who duped her offers to set them up if she pretends to be his own girlfriend for the holidays.



Career Opportunities

Josie, the daughter of the town's wealthiest businessman, faces problems at home and wishes to leave town but is disoriented. Her decision is finalized after she falls asleep in a Target dressing room. She awakens to find herself locked in the store overnight with the janitor, Jim, the town "no hoper" and liar.



In a Relationship
5.733

Long-term couple Owen and Hallie are breaking up—or maybe not?—and just as their relationship reaches a turning point, Matt and Willa embark on a romance of their own.



Holidate
Holidate(2020)
7

Fed up with being single on holidays, two strangers agree to be each other's platonic plus-ones all year long, only to catch real feelings along the way.



Press Play
6.562

Laura and Harrison have the picture-perfect romance built on the foundation of a shared love of music. After a deadly accident, Laura gets the chance to save the love of her life when she discovers that their mixtape can transport her back in time.



Unicorn Store
5.918

A woman named Kit moves back to her parent's house, where she receives a mysterious invitation that would fulfill her childhood dreams.



Two Can Play That Game

Corporate overachiever and all-around fly chick Shanté Smith thinks she's got the goods to keep her slickster boyfriend Keith, from straying—until he discovers a greener pasture, Shanté's archrival, Conny. Scorned, she plans to get her man back by any means necessary.



Focus
Focus(2015)
6.9

Nicky, an accomplished con artist, gets romantically involved with his disciple Jess but later ends their relationship. Years later, she returns as a femme fatale to spoil his plans.



The Right Kind of Wrong

A stubborn idealist spies a bride on her way to her wedding and immediately falls in love with her.



Friendzone
5.9

Hopeful romantic Thibault believes his luck could change when sparks fly between him and Rose. But can he go from bestie to boyfriend?



Management
5.365

A traveling art saleswoman tries to shake off a flaky motel manager who falls for her and won't leave her alone.



Yes Man
Yes Man(2008)
6.7

Carl Allen, a guy whose life is going nowhere, signs up for a self-help program based on one simple covenant: say yes to everything…and anything.



The Pill
The Pill(2011)
5.4

Worried that he has gotten the free-spirited Mindy pregnant after an unprotected one-night stand, Fred feigns romantic interest and sticks by her side for twelve hours to make sure she takes both doses of the morning-after pill.



Choose Love
4.8

The steady boyfriend. The one who got away. The charming rock star. Who will Cami choose? In this interactive rom-com, her love life is in your hands.



Flipped
Flipped(2010)
8

When Juli meets Bryce in the second grade, she knows it's true love. After spending six years trying to convince Bryce the same, she's ready to give up - until he starts to reconsider.



Love at Second Sight
7.051

A man tries to make his wife fall in love with him again, after waking up in an alternate reality where she never knew him.



Valentine's Day
5.924

Intertwining couples and singles in Los Angeles break-up and make-up based on the pressures and expectations of Valentine's Day.



Love at First Glance
5.697

After journalist Mary Landers is assigned to write a Valentine's Day story about "The Meaning of Love," her long-time boyfriend breaks up with her. On her train ride home, she finds herself trading glances with a handsome stranger who, as he exits the train, leaves his phone behind.



Chasing Amy
6.765

Holden and Banky are comic book artists. Everything is going good for them until they meet Alyssa, also a comic book artist. Holden falls for her, but his hopes are crushed when he finds out she's a lesbian.



Honeymoonish
6.718

Two newlyweds on their honeymoon discover that they are different in almost every way — but can these opposites attract?



Whatever It Takes
5.8

A nerdy teen, Ryan Woodman is smitten with the popular and gorgeous Ashley Grant, who apparently has no interest in him. Meanwhile, dim star athlete Chris Campbell has his eye on Ryan's brainy and beautiful friend, Maggie Carter. The two agree to help each other in their romantic quests, but, as they come closer to their goals, both Ryan and Chris suspect that they might be pursuing the wrong girls.



About Fate
7.505

Two strangers believe in love but never seem to be able to find its true meaning. In a wild twist of events, fate puts each in the other's path on one stormy New Year's Eve.



Dating Amber
7.1

Eddie and Amber decide to stage a relationship in order to stop everyone speculating about their sexuality. Eddie is keen to follow his dad into the military, while Amber dreams of moving to the liberal hub of London. The plan seems solid, but as their arrangement begins to fall apart, Eddie’s denial gets deeper as Amber realizes that a perilous future awaits her best friend unless she intervenes.



Hateship Loveship
5.811

A shy caretaker believes that the father of her teenage charge is falling in love with her, unaware that she is actually the victim of the girl's prank.



Arthur
Arthur(2011)
5.6

A drunken playboy stands to lose a wealthy inheritance when he falls for a woman that his family doesn't like.



About a Boy
6.685

Will Freeman is a good-looking, smooth-talking bachelor whose primary goal in life is avoiding any kind of responsibility. But when he invents an imaginary son in order to meet attractive single moms, Will gets a hilarious lesson about life from a bright, but hopelessly geeky 12-year-old named Marcus. Now, as Will struggles to teach Marcus the art of being cool, Marcus teaches Will that you're never too old to grow up.



Time Freak
6.697

Stillman, a heartbroken physics student, builds a time machine when his girlfriend breaks up with him. Going back in time, he attempts to save their relationship by fixing every mistake he made—while dragging his best friend along in the process.



Dater's Handbook
5.619

A woman changes her personality according to a dating guide book to find a husband but realizes the man she wants is the one who loves her for who she is.



Ruby Sparks
7.112

Calvin is a young novelist who achieved phenomenal success early in his career but is now struggling with his writing – as well as his romantic life. Finally, he makes a breakthrough and creates a character named Ruby who inspires him. When Calvin finds Ruby, in the flesh, sitting on his couch about a week later, he is completely flabbergasted that his words have turned into a living, breathing person.



Fingernails
5.957

Anna and Ryan have found true love together. It's been proven by a controversial test. There's just one problem: Anna still isn't sure. Then she meets Amir.



Warm Bodies
6.5

After a zombie becomes involved with the girlfriend of one of his victims, their romance sets in motion a sequence of events that might transform the entire lifeless world.



Frequencies
6.5

The story of the forbidden relationship between a 'low born' boy and a 'high born' girl in an alternate reality where every person's relationships and life worth are determined by their innate 'frequencies'.



Love Wedding Repeat
5.644

While trying to make his sister's wedding day go smoothly, Jack finds himself juggling an angry ex-girlfriend, an uninvited guest with a secret, a misplaced sleep sedative, and the girl that got away in alternate versions of the same day.



Date Movie
4.3

Spoof of romantic comedies which focuses on a man, his crush, his parents, and her father.



Lucas
Lucas(1986)
6.7

A brilliant but socially inept 14-year-old experiences heartbreak for the first time when his two best friends – Cappie, an older-brother figure, and Maggie, the new girl with whom he is in love – fall for each other.



Wedding Daze
5.568

After losing the woman of his dreams, Anderson is convinced he'll never fall in love again. But at the urging of his best friend, he spontaneously proposes to a dissatisfied waitress named Katie and an innocent dare evolves into the kind of love that both have been looking for all along.



Players
Players(2024)
6.082

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.



Happy Ending
5.821

A young woman quietly unsatisfied in the bedroom by her boyfriend puts their relationship to the test when she proposes to open up their sex life to a third person.



My Best Friend's Wedding

When she receives word that her longtime platonic pal Michael O'Neal is getting married to debutante Kimberly Wallace, food critic Julianne Potter realizes her true feelings for Michael -- and sets out to sabotage the wedding.



A Romantic Comedy
4.63

Bored with her life and inspired by a friend's wedding, Esra quits her job and dumps her boyfriend, leading to a series of romantic misadventures.



As If It Were the First Time

A man falls in love with a girl who has short-term memory loss.



Lo
Lo(2009)
6.6

Love presents many challenges to couples...but none so daunting as the one Justin faces with his girlfriend April...



Life Like
Life Like(2019)
6.2

An idealistic attractive young couple acquires a stunning, life-like robot for guilt free help, but as the three grow closer, their perception of humanity will be altered forever.



Arthur Newman
5.6

A story of a man who fakes his own death and assumes a new identity in order to escape his life, who then moves in with a woman who is also trying to leave her past behind.



One True Loves
6.3

Emma and Jesse are living the perfect life together, until Jesse disappears in a tragic helicopter crash on their first wedding anniversary. Four years later, Emma has found happiness again and is about to marry her best friend when Jesse resurfaces, turning her world upside down and leaving her torn between two great loves.



Some Freaks
6.136

A charming romance develops between a boy with one eye and an overweight girl, though when she loses weight after going to college, their relationship is tested in devastating ways they never dreamed would happen.



Say It Isn't So
4.7

Boy meets girl; boy falls in love (and had wild, non-stop sex) with girl; boy loses girl... when they discover they are brother and sister! But when he learns that he's the victim of the ultimate case of mistaken identity, the lovesick young man -- whom everyone still thinks is after some taboo thrills -- must race across the country to stop her from marrying another man.



Music and Lyrics
6.4

A washed-up '80s pop star gets a chance at a comeback when reigning pop diva Cora Corman invites him to write & record a duet with her, but there's a problem--Alex hasn't written a song in years; he's never written lyrics and he has to come up with a hit in a matter of days.



A Lot Like Love
6.8

On a flight from Los Angeles to New York, Oliver and Emily make a connection, only to decide that they are poorly suited to be together. Over the next seven years, however, they are reunited time and time again, they go from being acquaintances to close friends to... lovers?



Results
Results(2015)
5.048

Two mismatched personal trainers' lives are upended by the actions of a new, wealthy client.



Vamps
Vamps(2012)
5.348

The modern-day story focuses on two beautiful young vampires who are living the good nightlife in New York until love enters the picture and each has to make a choice that will jeopardize their immortality.



Punch-Drunk Love
7.1

A socially awkward and volatile small business owner meets the love of his life after being threatened by a gang of scammers.



Kids in Love
5.752

Drifting through his gap year with its internships and travel plans, Jack has always suspected there was more to life than this. A chance encounter with the beautiful and ethereal Evelyn swerves his life radically off course.



SPF-18
SPF-18(2017)
4.423

Eighteen-year-old Penny Cooper spent years pining for heartthrob surfer Johnny Sanders Jr. before his father’s tragic death brought them closer together. But now high school is over, and when mysterious country musician Ash Baker shows up on the beach, Penny is torn.



Winter Spring Summer or Fall

Remi and Barnes, two very different teenagers, meet by chance in the winter of their senior year, then spend four days together over the course of a year that will change their lives forever.



Overnight Delivery
5.545

A man suspects his girlfriend of being unfaithful, so he sends her a letter, but then finds out that he was wrong. He has 24 hours to stop the package, prevent a disaster, and fall in love. The only problem is the delivery man will not stop until the package has been delivered.



Spellbound
7.5

A magician meets a weird girl and offers her to work together in his magic show. It's only until a year later that he starts to know her personally and develops a feeling towards her despite her own problems.



Waiting for Forever

A Hollywood-set romantic tale of a guy who is content to live his life without a job yet with the love of his life, a young actress.



Endless Love
5.7

As their romance unfolds, Jade and David's growing love for one another becomes the scorn of Jade's father. However, when Jade's grades begin to drop, her father forbids the young couple from seeing each other for 30 days. Driven insane with frustration and desire, David attempts to reverse the decision, with catastrophic results.



Submarine
Submarine(2011)
7.365

15-year-old deep-thinking Welsh schoolboy Oliver Tate struggles to initiate and maintain a relationship with Jordana, his devilish, dark-haired classmate at their Swansea high school. As his parents' marriage begins to fall apart, similar problems arise in his relationship with Jordana.



Ellie and Abbie (and Ellie's Dead Aunt)

School captain Ellie is seriously crushing on her rebellious classmate Abbie. Determined to ask her first love to the year 12 formal, Ellie devises a plan to go public with the invitation but before she can go through with it, her dead aunt Tara reappears from beyond the grave. Believing she's been brought back from the dead to be Ellie's fairy godmother, Tara dishes out unwanted dating advice based on her life as an out lesbian in the '80s.



Laggies
Laggies(2014)
6.1

Overeducated and underemployed, 28 year old Megan is in the throes of a quarterlife crisis. Squarely into adulthood with no career prospects, no particular motivation to think about her future and no one to relate to, Megan is comfortable lagging a few steps behind - while her friends check off milestones and celebrate their new grown-up status. When her high-school sweetheart proposes, Megan panics and- given an unexpected opportunity to escape for a week - hides out in the home of her new friend, 16-year old Annika and Annika's world-weary single dad Craig.



Hitch
Hitch(2005)
6.6

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.



Trainwreck
5.799

Having thought that monogamy was never possible, a commitment-phobic career woman may have to face her fears when she meets a good guy.



Fanfic
Fanfic(2023)
6.96

Two high school students form an intense connection as they navigate the challenges of discovering and expressing their truest selves.



Love Don't Co$t a Thing

A high school outcast pays a cheerleader to pose as his girlfriend so he can be considered cool.



Aloha
Aloha(2015)
5.5

A celebrated military contractor returns to the site of his greatest career triumphs and re-connects with a long-ago love while unexpectedly falling for the hard-charging Air Force watchdog assigned to him.



Everything, Everything

A teenager who's lived a sheltered life because she's allergic to everything, falls for the boy who moves in next door.



Love Untangled
8.427

A lovestruck teen plans to win the school heartthrob by going from curly to straight hair — until a new transfer student changes everything.



Molly Maxwell
6.623

At Phoenix Progressive School, students take notes lying on parlor couches and are encouraged to explore their gifts through electives like break-dancing and graphic-novel writing. In the midst of all this liberal pedagogy and budding talent, Molly Maxwell feels unexceptional, until she falls for her attractive English teacher, Ben.



The Oh in Ohio
5.213

Frustrated with their relationship, Priscilla and Jack decide to take a break. While Jack moves into a new place of his own and starts dating a student, Priscilla discovers the joys of self-pleasuring and finds an unusual bedmate.



Keith
Keith(2008)
7.042

Natalie is high school royalty, but her queen bee status falls apart when she falls for the new guy at school. Although Keith ignores her at first, they soon become friends -- even though Natalie suspects that Keith has something to hide. As the free-spirited Keith shows Natalie how to embrace what life offers, they grow closer -- until a secret tests the bounds of their relationship

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