Playing It Cool

Watch Trailer Watch Movie

Playing It Cool

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

2014

1h 34m

5.8(814 votes)

Comedy

Romance

Overview

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

Links & Resources

IMDbView

Social & External

IMDb

Production Companies

Videos & Trailers

1 video

Cast & Crew

22 members

Acting

Chris Evans

Narrator

Acting

Michelle Monaghan

Her

Acting

Topher Grace

Scott

Acting

Aubrey Plaza

Mallory

Acting

Luke Wilson

Samson

Acting

Martin Starr

Lyle

Acting

Anthony Mackie

Bryan

Acting

Ioan Gruffudd

Stuffy

Acting

Philip Baker Hall

Granddad

Acting

Patrick Warburton

Dick

Acting

Ashley French

Ashley Tisdale

Acting

Matthew Morrison

Acting

Jaeden Martell

6 Year Old Me

Acting

Fabianne Therese

College Girl

Acting

Gerry Bednob

Cabbie / Gabriel

Acting

Beverly D'Angelo

Lyle's Girlfriend

Acting

Kyle Mooney

Other Dude

Acting

Scott Evans

Blissful Boy

Acting

Brenda Schmid

Blissful Girl

Acting

Sarah Dumont

Cute Girl

Acting

Mikaela Hoover

Lacey

Acting

Devon Ogden

Sadie

Similar Movies

6.2

2007

2 Days in Paris

Marion and Jack try to rekindle their relationship with a visit to Paris, home of Marion's parents — and several of her ex-boyfriends.

Movie

7.5

1939

Ninotchka

A stern Russian woman sent to Paris on official business finds herself attracted to a man who represents everything she is supposed to detest.

Movie

7.1

2014

INT. CAFÉ – NIGHT

A short film exploring two stories about love, loss and reunion set inside a café in Kolkata, India.

Movie

5.7

2022

Someday or One Day

In 2009, 28-year-old Li Zi Wei and 17-year-old Huang Yu Xuan met each other. These are two innocent and unaffected lives that could each feel like marks from their past and present lives. However, they could not find sufficient proof to fill up the emptiness at the bottom of their hearts. An accident let them fall into another Mobius loop that had already happened countless times. Only then did they realize that in different times and spaces, they once had a deep, true love that had passed through countless timelines to search for each other with no regrets. But in that story, their deepest love came at the highest price. If they could start again, would they choose to meet by chance in ordinary life or be scarred by the memories etched in their heart and bones? Or perhaps they can choose to hurt and love all over again, betting on a different ending?

Movie

4.5

2013

Vedivazhipadu

Three friends decide to hire a prostitute on the day of the Aatukaal Pongala - a Hindu festival in Trivandrum - when their wives are busy.

Movie

7.1

1985

Re-Animator

Conducting clandestine experiments within the morgue at Miskatonic University, scientist Herbert West reveals to a fellow graduate student his groundbreaking work concerning the re-animation of fresh corpses.

Movie

6.9

2004

50 First Dates

Henry is a player skilled at seducing women. But when this veterinarian meets Lucy, a girl with a quirky problem when it comes to total recall, he realizes it's possible to fall in love all over again…and again, and again. That's because the delightful Lucy has no short-term memory, so Henry must woo her day after day until he finally sweeps her off her feet.

Movie

5.3

2000

The Next Best Thing

A comedy-drama about best friends - one a straight woman, Abbie, the other a gay man, Robert - who decide to have a child together. Five years later, Abbie falls in love with a straight man and wants to move away with her and Robert's little boy Sam, and a nasty custody battle ensues.

Movie

6.9

1972

Last Tango in Paris

A recently widowed American begins an anonymous sexual relationship with a young Parisian woman.

Movie

7.5

1962

Jules and Jim

In the carefree days before World War I, introverted Austrian author Jules strikes up a friendship with the exuberant Frenchman Jim and both men fall for the impulsive and beautiful Catherine.

Movie

5.4

2003

Stuck on You

In Martha's Vineyard, Mass., conjoined twins Walt and Bob Tenor make the best of their handicap by being the fastest grill cooks in town. While outgoing Walt hopes to one day become a famous actor, shy Bob prefers to stay out of the spotlight. When a fading Hollywood actress, Cher, decides to get her show "Honey and the Beaze" cancelled, she hires Walt -- and his brotherly appendage -- as her costars. But their addition surprisingly achieves the opposite.

Movie

6.6

2005

Russian Dolls

Five years after their summer together in Barcelona, Xavier, William, Wendy, Martine and Isabelle reunite.

Movie

6.1

2004

In Good Company

Dan Foreman is a seasoned advertisement sales executive at a high-ranking publication when a corporate takeover results in him being placed under naive supervisor Carter Duryea, who is half his age. Matters are made worse when Dan's new supervisor becomes romantically involved with his daughter an 18 year-old college student Alex.

Movie

6.8

2001

Vanilla Sky

David Aames has it all: wealth, good looks and gorgeous women on his arm. But just as he begins falling for the warmhearted Sofia, his face is horribly disfigured in a car accident. That's just the beginning of his troubles as the lines between illusion and reality, between life and death, are blurred.

Movie

6.8

1994

Don Juan DeMarco

John Arnold DeMarco is a man who believes he is Don Juan, the greatest lover in the world. Clad in a cape and mask, DeMarco undergoes psychiatric treatment with Dr. Jack Mickler to cure him of his apparent delusion. But the psychiatric sessions have an unexpected effect on the psychiatric staff and, most profoundly, Dr Mickler, who rekindles the romance in his complacent marriage.

Movie

6.4

2020

Alice Júnior

This is the story of Alice Junior, a transgender girl full of life, who wants to give her first kiss, but first, she just wants to be who she really is.

Movie

3.0

2023

Mexican Standoff

Movie adaptation of a very famous local podcast show of Meksika Açmazi. In this show, 3 famous Turkish comedian Mesut Süre, AnlatanAdam and Fazli Polat discuss wide range of daily issues we are facing and look at the situation in very different aspects.

Movie

8.7

1975

The Happy Couple

A comedy about life during the 1970's. A father refuses to accept his son marrying a girl from a different religion, thus leading to several comical situations.

Movie

Perfect Day

The journey of a boy accepting that his lover is gone

Movie

6.8

1997

Nowhere

In Los Angeles, a colorful assortment of bohemians try to make sense of their intersecting lives. The moody Dark Smith, his bisexual girlfriend, her lesbian lover and their shy gay friend plan on attending the wildest party of the year. But they'll only make it if they can survive the drug trips, suicides, trysts, mutilations and alien abductions that occur as one surreal day unfolds.

Movie

Recommended Movies

8.4

2026

Voicemails for Isabelle

A young woman's hilariously confessional voicemails to her late sister are unknowingly redirected to a stranger, who begins to fall in love from afar.

Movie

8.5

2023

¿Quieres ser mi hijo?

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.

Movie

6.0

2001

Someone Like You...

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.

Movie

6.1

2024

Players

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.

Movie

6.4

2019

Someone Great

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.

Movie

6.4

2024

How to Date Billy Walsh

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.

Movie

6.0

2025

Picture This

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.

Movie

6.3

2024

French Girl

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.

Movie

6.0

2020

Desperados

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.

Movie

6.8

2008

My Sassy Girl

A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.

Movie

6.4

1979

Starting Over

After divorcing his ambitious singer wife, a middle-aged man begins a new relationship with a teacher.

Movie

6.6

2022

Sex Appeal

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.

Movie

6.7

2023

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, Percy, before he leaves for college. To her surprise, Maddie soon discovers the awkward Percy is no sure thing.

Movie

7.0

2023

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 on the way! The hilariously mismatched Nicole and Max are forced to become responsible co-parents, but may end up finding love themselves.

Movie

6.3

2022

I Want You Back

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.

Movie

6.5

2009

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 and help her find love. His clever ploys, however, lead to an unexpected result.

Movie

6.0

2014

About Last Night

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.

Movie

6.6

2022

Bros

Two gay men are possibly, probably, stumbling towards love. Maybe. They're both very busy.

Movie

6.0

1989

How I Got Into College

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.

Movie

6.2

1984

The Lonely Guy

A writer for a greeting card company learns the true meaning of loneliness when he comes home to find his girlfriend in bed with another man.

Movie