Playing It Cool

Playing It Cool

Playing It Cool

Watch Trailer Watch Movie

Share

Playing It Cool

"Love... it's a balancing act"

2014

1h 34m

5.8(799 votes)

Comedy

Romance

Overview

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

Where to Watch

Stream

Amazon Prime Video

Amazon Prime Video with Ads

Links & Resources

Social & External

Production Companies

Wonderland Sound and Vision

Voltage Pictures

Videos & Trailers

1 video

Cast & Crew

22 members

Acting

Chris Evans

Narrator

Chris Evans

Acting

Michelle Monaghan

Her

Michelle Monaghan

Acting

Topher Grace

Scott

Topher Grace

Acting

Aubrey Plaza

Mallory

Aubrey Plaza

Acting

Luke Wilson

Samson

Luke Wilson

Acting

Martin Starr

Lyle

Martin Starr

Acting

Anthony Mackie

Bryan

Anthony Mackie

Acting

Ioan Gruffudd

Stuffy

Ioan Gruffudd

Acting

Philip Baker Hall

Granddad

Philip Baker Hall

Acting

Patrick Warburton

Dick

Patrick Warburton

Acting

Ashley French

Ashley Tisdale

Ashley French

Acting

Matthew Morrison

Matthew Morrison

Matthew Morrison

Acting

Jaeden Martell

6 Year Old Me

Jaeden Martell

Acting

Fabianne Therese

College Girl

Fabianne Therese

Acting

Gerry Bednob

Cabbie / Gabriel

Gerry Bednob

Acting

Beverly D'Angelo

Lyle's Girlfriend

Beverly D'Angelo

Acting

Kyle Mooney

Other Dude

Kyle Mooney

Acting

Scott Evans

Blissful Boy

Scott Evans

Acting

Brenda Schmid

Blissful Girl

Brenda Schmid

Acting

Sarah Dumont

Cute Girl

Sarah Dumont

Acting

Mikaela Hoover

Lacey

Mikaela Hoover

Acting

Devon Ogden

Sadie

Devon Ogden

Similar Movies

Love Hina Christmas Special: Silent Eve

Love Hina Christmas Special: Silent Eve

As another round of preliminary tests approach for Keitarō, so does Christmas. And as the first Christmas of the millennium, there is a rumor that if one confesses his love on this special eve it will come true. Keitarō has decided what he needs to do on this Christmas eve. But being a retaker, can he afford taking attention away from the tests on the same day?

Letters to Juliet

Letters to Juliet

An American girl on vacation in Italy finds an unanswered "letter to Juliet" -- one of thousands of missives left at the fictional lover's Verona courtyard, which are typically answered by the "secretaries of Juliet" -- and she goes on a quest to find the lovers referenced in the letter.

Sailor Moon R: The Movie - The Promise of the Rose

Sailor Moon R: The Movie - The Promise of the Rose

While enjoying the flower gardens, Sailor Moon and friends encounter an old childhood friend of Mamoru's: an alien! He's come back to give Mamoru a special flower but doesn't like Usagi and the rest of the planet's inhabitants. Sailor Moon must defend the earth from the evil Kisenian Flower he's brought back... before the evil vines and blossoms overrun the planet!

Jolly Fellows

Jolly Fellows

Merry Fellows was the first Soviet musical comedy. Set in Odessa and Moscow in the 1930s. Shepherd Kostya Potekhin (Utyosov) is mistaken for an international concert star. He falls in love with Anyuta (Orlova) and plays the "star" for her. In a cascade of comic musical numbers he becomes the leader of a Jazz-Band and gives a hilarious show at the Odessa Music Hall. Now he is destined to perform at the Bolshoi Theatre in Moscow.

Only Old Men Are Going to Battle

Only Old Men Are Going to Battle

Alexey Titarenko is very talented pilot and brave leader of "Singing group". He also must look after some new cadets and fight together with them against German Luftwaffe planes. Close to Alexey always are his friends, they are all from different parts of the country, but they all became real brothers.

The Naked Gun: From the Files of Police Squad!

The Naked Gun: From the Files of Police Squad!

When the bumbling Lieutenant Frank Drebin investigates events following the shooting of his partner, he stumbles upon an attempt to assassinate Queen Elizabeth II.

The Naked Gun 2½: The Smell of Fear

The Naked Gun 2½: The Smell of Fear

Bumbling lieutenant Frank Drebin is out to foil the big boys in the energy industry, who intend to suppress technology that will put them out of business.

Reservations

Reservations

Due to a glitch in the reservation system, seven strangers must compete before the Gods of War, aka Susan, for a place to stay.

Poppay Ki Wedding

Poppay Ki Wedding

A contemporary boy returns to his traditional hometown for his sister's wedding, soon discovering his own proposal finalized with a girl he's never seen. Challenging family customs, his sole mission is to at least see the face of his future bride-to-be.

Me and My Girl

Me and My Girl

Recording of the Takarazuka Revue's 2008 Moon Troupe production of the musical "Me and My Girl."

Manhattan Romance

Manhattan Romance

Danny, a commercial editor and documentary filmmaker attempts to finish his film, a study on relationship while navigating the relationships in his own life. Will he continue to chase the unattainable Theresa a hippy new age dancer(Caitlin Fitzgerald) or will he finally admit he's in love with his best friend Carla (Katherine Waterston) who is in an unfulfilling relationship with a political strategist(Gaby Hoffman). Manhattan Romance is a funny insightful look at contemporary life in Manhattan. It explores new age ideas and open relationship as well as true friendship and connection.

Trust

Trust

After being thrown away from home, pregnant high school dropout Maria meets Matthew, a highly educated and extremely moody electronics repairman. The two begin an unusual romance built on their sense of mutual admiration and trust.

Na układy nie ma rady

Na układy nie ma rady

When Marek Niewiadomski gets a proposal, which is the job of another deputy minister in one of the state departments, his current life is changing. All decisions he must make with his wife to be an honest citizen bring him many challenges. There is no cure for deals.

Dazzling Mirage

Dazzling Mirage

An adaptation of Yinka Egbokhare's novel. The story of a young sickle-cell patient and the various social and emotional challenges she's faced with.

Sorry if I Love You

Sorry if I Love You

Alex Belli is a 37 year old advertising executive whose fiancée Elena has just left him, and who is having difficulty at work trying to think of a good advertising campaign for a new Japanese product. Niki is a bubbly 17 year old student. She has three best friends with whom she shares all her problems, and an annoying ex-boyfriend Fabio who is set on getting her back, but Niki's not interested. One day on his way to work, Alex collides with Niki on a city street. They soon begin a romance, despite their 20-year age gap.

Doug Stanhope: Deadbeat Hero

Doug Stanhope: Deadbeat Hero

In "Deadbeat Hero," Stanhope tackles all of the most relevant and controversial issues of our times: Abortion, "liberty," war, whether blindly supporting the troops is a good thing, the drug war, the Alabama-Mississippi ban on dildos and other sex toys, gay marriage and priest molestations. More bizarre topics include two-head babies, his suicidal cat-lady mother, and more.

Casual Sex?

Casual Sex?

Two girls go away to a holiday resort looking for a change of pace, hoping to meet some nice men for a change. They discover that they can't find the perfect man, and this forces them to reconsider their attitudes to men in general.

A Wonderful Christmas Time

A Wonderful Christmas Time

A young man and young woman, both who have recently gone through break-ups, become friends over the festive season though don't wish to be each other's respective rebound. To get over this, the man goes on a series of disastrous dates so he can get together with the girl he really likes.

So Different

So Different

Single mother Lotta and her younger sister Sanna are both successful in their different jobs, and are living very different lives, but are attracted to men who are their opposites.

Ranma 1/2 the Movie: Big Trouble in Nekonron, China

Ranma 1/2 the Movie: Big Trouble in Nekonron, China

When Prince Kirin of the 7 Lucky Gods shows up at the Tendo dojo looking for his bride-to-be, guess who's accidentally holding the scroll that signifies his future mate? Why, Akane, of course, and the rest of the Ranma crew is forced to take a boat to China in order to save her from the horrors of marriage and a diet of pickled vegetables.

Recommended Movies

Puncture

Puncture

A lawyer who is a drug addict fights a medical-supplies corporation in court while battling his personal demons.

The Driftless Area

The Driftless Area

Pierre Hunter, a bartender with unyielding optimism, returns to his tiny hometown after his parents' death. When he falls for the enigmatic Stella, Pierre is unknowingly pulled into a cat-and-mouse game that involves a duffel bag full of cash, a haphazard yet determined criminal, and a mystery that will determine all of their fates. A contemporary fable about the ways we struggle to control time and fate in a possibly predetermined universe.

Air Bridge

Air Bridge

Bruno and Amanda have to face the difficulties of a long distance relationship after meeting in a flight forced into an emergency landing.

For Lovers Only

For Lovers Only

An American photographer runs into an old flame while on assignment in Paris.

The Other End

The Other End

Diogo (17) has a little quirk: he likes to call his mother's female therapy patients and masturbate while listening to them on the phone. One of these patients is Angela (43), a woman who was just left by her husband When Diogo calls Angela, she thinks it's her husband calling. She starts having a relationship with the silence on the other end of the line. But when she finds out it's Diogo, she's disgusted. She's furious. But, most of all, she's attracted to this person who showed so much interest in her. The only person who called her every day. Diogo helps Angela see that she can have a new beginning and she shows him his way to independence. But they have to face a number of obstacles: There's the age difference, Diogo's mother, and, especially, his own path to adulthood.

Riocorrente

Riocorrente

Marcelo is a journalist. Carlos is a former car-thief. Renata is a woman torn apart by two relationships as diverse as her desires. Exu is the ever becoming.

Kundo: Age of the Rampant

Kundo: Age of the Rampant

In 1862, amidst the rule of the late Joseon dynasty in Korea, a band of fighters named Kundo rise against the unjust authorities.

The Innocence

The Innocence

Lis is a teenager whose dream is to become a circus artist and leave her hometown, even if she knows that to do it she’ll have to fight her side against her parents. It’s summer and she spends her days playing with her friends and flirting with her boyfriend, a few years older than herself. The lack of privacy and the neighbours’ gossip force Lis to keep their relationship secret so that her parents won’t find out. A relationship which change her live forever.

Doctor Who: Deep Breath

Doctor Who: Deep Breath

The newly-regenerated Doctor arrives in Victorian London, and Clara Oswald struggles to embrace the man he has become. All the while, they reunite with the Paternoster Gang to investigate a series of combustions that have been occurring all around the city.

Loucas pra Casar

Loucas pra Casar

Malu, Lúcia and Maria found the ideal man to marry. Until they discover that in reality this man is the same person: Samuel, who was dating all of them over the past years. The three will have to decide if they will fight amongst each other for exclusivity or will unite in revenge.

Copenhagen

Copenhagen

After weeks of traveling through Europe, the immature William finds himself in Copenhagen, the place of his father’s birth. He befriends the youthful Effy, who works in William’s hotel as part of an internship program, and they set off to find William’s last living relative. Effy’s mix of youthful exuberance and wisdom challenges William unlike any woman ever has. As the attraction builds, he must come to grips with destabilizing elements of his family’s sordid past.

Staten Island Summer

Staten Island Summer

Pals Danny and Frank spend the summer after high school working as lifeguards while figuring out their future.

Ever Been to the Moon?

Ever Been to the Moon?

Giulia is 30, single and working a high-end fashion job that allows her to travel and lead a dream life in Milan and Paris. However, a chance meeting with charming, down-to-earth farmer Renzo will makes her realize she's missing the most important thing in life—true love.

Welcome to Me

Welcome to Me

A year in the life of Alice Klieg, a woman with Borderline personality disorder who wins the Mega Millions lottery, quits her meds and buys her own talk show.

Watching the Detectives

Watching the Detectives

Neil, a self-proclaimed film geek and owner of Gumshoe video, has always been content to live vicariously through his favorite films noir. But when he meets Violet, a real-life femme fatale, his mundane world gets turned upside down and the line between reality and the movies quickly begins to blur.

Walk. Ride. Rodeo.

Walk. Ride. Rodeo.

Tells the incredible true story of Amberley Snyder, a nationally ranked rodeo barrel racer who defies the odds after barely surviving a car accident that leaves her paralyzed from the waist down.

Frequencies

Frequencies

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'.

Laggies

Laggies

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.

Brad's Status

Brad's Status

Although Brad has a satisfying career, a sweet wife and a comfortable life in suburban Sacramento, things aren't quite what he imagined during his college glory days. When he accompanies his musical prodigy son on a university tour, he can't help comparing his life with those of his four best college friends who seemingly have more wealthy and glamorous lives. But when circumstances force him to reconnect with his former friends, Brad begins to question whether he has really failed or if their lives are actually more flawed than they appear.

Two Night Stand

Two Night Stand

After an extremely regrettable one night stand, two strangers wake up to find themselves snowed in after sleeping through a blizzard that put all of Manhattan on ice. They're now trapped together in a tiny apartment, forced to get to know each other way more than any one night stand should.