Playing It Cool

Watch Trailer Watch Movie

Playing It Cool

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

2014

1h 34m

5.8(802 votes)

Comedy

Romance

Overview

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

Where to Watch

Stream

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

5.6

2005

Rebound

An acclaimed college hoops coach is demoted to a junior varsity team after a public meltdown.

Movie

7.5

2016

Love Everlasting

Bridger is a young outsider who's always wanted more. He and his mother flee an abusive home, eventually finding a small town in the middle of nowhere. Once there, Bridger finds true acceptance with another misfit.

Movie

5.4

2017

The Lovers

The separation of a long married couple goes awry when they fall for each other again.

Movie

5.9

2005

Sahara

Seasoned adventurer and treasure hunter Dirk Pitt, a former Navy SEAL, sets out for the African desert with his wisecracking buddy Al in search of a confederate ironclad battleship rumored to have vanished long ago, the main draw being the treasure supposedly hidden within the lost vessel. When the daring duo come across Dr. Eva Rojas, a beautiful scientist who is juggling an escape from a warlord and a mission to stop the spread of a powerful plague, their desert expedition begins to heat up.

Movie

6.7

2008

Tropic Thunder

A group of self-absorbed actors set out to make the most expensive war film ever. After ballooning costs force the studio to cancel the movie, the frustrated director refuses to stop shooting, leading his cast into the jungles of Southeast Asia, where they encounter real bad guys.

Movie

5.6

2005

Side Effects

America! Built on a better pill. Karly Hert has spent the last ten years selling drugs. Legally, that is. Karly is a pharmaceutical sales representative. She sells pills to doctors. She makes lots of money. She has a company car. She has a nice fat expense account. But there's a growing pit in Karly's stomach. Something isn't right behind the scenes at big pharma. Based on the director's decade working directly for the industry.

Movie

7.1

2002

Punch-Drunk Love

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

Movie

1938

Jane Steps Out

Wallflower Jane Wilton has always lived in the shadow of her beautiful and popular sister Beatrice. Making things worse, Beatrice is spiteful and cruel, directing all manner of nastiness towards the submissive and uncomplaining Jane. But when Beatrice sets her cap for Jane's erstwhile boy friend Basil Gilbert, she goes a shade too far. For once, the worm turns, and Jane fights tooth and nail to win her man back. A retelling of the Cinderella story.

Movie

1933

Sailor Be Good

A Navy boxer (Jack Oakie) meets a dance-hall hostess (Vivienne Osborne) who tries to sober him up for a fight.

Movie

1946

Sing While You Dance

Susan Kent, hoping to establish herself as a song-plugger, tries to obtain a second song from a young songwriter, Johnny Crane, after his first song becomes a hit. While pursuing her objective, she falls in love with Johnny, and lands in jail, but she acquires the song, the job, and Johnny.

Movie

5.4

2006

Come Early Morning

A thirty-something southern woman searches for love, despite the burdens she carries with her.

Movie

5.6

2006

Wedding Daze

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.

Movie

6.4

2007

Outsourced

After his entire department is outsourced, an American novelty products salesman heads to India to train his replacement.

Movie

6.1

1997

A Life Less Ordinary

A couple of angels, O'Reilly and Jackson, are sent to Earth to make sure that their next supervised love-connection succeeds. They follow Celine, a spoiled rich girl who has just accidentally shot a suitor and, due to a misunderstanding, is kidnapped by janitor Robert. Although Celine quickly frees herself, she stays with Robert for thrills. O'Reilly and Jackson pursue, hoping to unite the prospective lovers.

Movie

4.0

2018

Love 'N' Oven

On Love N Oven, we break down a scenario in a relationship and make a dish perfect for the occasion.

Movie

7.0

2014

The Plan Man

The Plan Man is about a man who lives everything according to plan until he meets a woman who wasn't a part of it.

Movie

10.0

2020

Petalers

A young fella has a case of the butterflies. With nothing but the clothes on his back and a flower for a lovely lady, the flower takes priority.

Movie

5.8

2006

Failure to Launch

At 35, Tripp has an interesting job, a hip car, a passion for sailing, an active dating life, and a great house - trouble is, he still lives with his parents, Al and Sue, who are not happy about it. Al and Sue are fascinated when friends whose adult son has recently moved away from home reveal they hired an expert to help. In desperation to push Tripp out of the nest once and for all, Al and Sue hatch a plan to hire Paula, an "interventionist," who has a formula in these cases.

Movie

7.5

1954

Sabrina

After her return from school in Paris, a playboy finally takes notice of his family's chauffeur's daughter Sabrina, who's long had a crush on him, but he questions his more serious brother's motives when he warns against getting involved with her.

Movie

6.8

2014

The Little House

Following the death of the unmarried and childless Taki, Takeshi, a young relative of hers, discovers several pages of closely written lines in which the old lady has recorded her memories. This is how he learns the truth about her youth working as a housemaid and nanny for the Hirai family in a little house in Tokyo with a red gabled roof.

Movie

Recommended Movies

6.0

2023

The List

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.

Movie

6.7

2025

The Wrong Paris

Dawn thinks she's joining a dating show in Paris, France, only to land in Paris, Texas. She has an exit plan — until sparks fly with the cowboy bachelor.

Movie

7.4

2011

One Day

A romantic comedy centered on Dexter and Emma, who first meet during their graduation in 1988 and proceed to keep in touch regularly. The film follows what they do on July 15 annually, usually doing something together.

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

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

5.9

2006

Catch and Release

For a grieving fiancée, learning to love again requires the help of her late love's three best friends.

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

6.0

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

5.9

2010

Valentine's Day

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

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

7.6

2020

The Kissing Booth 2

With college decisions looming, Elle juggles her long-distance romance with Noah, changing relationship with bestie Lee and feelings for a new classmate.

Movie

6.1

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

5.9

1994

Speechless

In the midst of election season in New Mexico, political speechwriters Julia Mann and Kevin Vallick begin a romance, unaware they are working for candidates on opposite sides.

Movie

6.1

2017

Newness

In contemporary Los Angeles, two millennials navigating a social media–driven hookup culture begin a relationship that pushes both emotional and physical boundaries.

Movie

6.7

2008

Yes Man

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.

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

6.1

2014

Top Five

Though he began in stand-up comedy, Andre Allen hit the big-time as the star of a trilogy of action-comedies about a talking bear but now he wants to be taken seriously. His passion project about the Haitian Revolution, a movie called Uprize, was panned by the NY Times film critic. A couple days before the wedding to his reality star fiancée, he's forced to spend the day with Chelsea Brown, a profile writer for the New York Times. Unexpectedly, he opens up to her, and as they wind their way across New York, he tries to get back in touch with his comedic roots.

Movie

6.2

1984

The Woman in Red

When a happily married family man, who would never consider an affair, meets a beautiful woman in red, he is totally infatuated and desperate to make her acquaintance. However, as he tries out various schemes to sneak out to meet her, he realizes that adultery is not quite as easy as it looks.

Movie

6.1

2023

Which Brings Me to You

Two romantic burnouts, Jane and Will, are immediately drawn to each other at a mutual friend’s wedding. After a disastrous hookup in the coatroom, the two spend the next 24 hours together, trading candid confessions of messy histories and heartbreak, on the off chance that this fling might be the real thing.

Movie

5.9

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