Backdrop fallback

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(813 votes)

Comedy

Romance

Overview

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

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

3 Ninjas Kick Back

3 Ninjas Kick Back

During a championship baseball match, the three brothers hear that their grandfather in Japan is in trouble, and head out to help him, conceding the match. When they arrive in Japan, they must use all their powers to defend him against his ancient enemy, who has returned to exact revenge.

Love at First Bite

Love at First Bite

Dracula and Renfield relocate to '70s era New York in search of Cindy Sondheim, the reincarnation of Dracula's one true love, Mina Harker. "Trouble adjusting" is a wild understatement for the Count as he battles Cindy's psychiatrist, Jeffrey Rosenberg, a descendant of Van Helsing, who may be in love with Cindy too.

Boldly Go

Boldly Go

A young gay man is hiding an embarrassing secret about his body. When a long-term crush begins seducing him at a party, he is forced to confront his shame and expose the truth, or risk losing the boy of his dreams.

Table for Three

Table for Three

A suddenly single guy invites what he thinks is a perfect couple to move into his apartment, only to discover they quickly insert themselves into all aspects of his life.

30 Days Until I'm Famous

30 Days Until I'm Famous

A Latina working in Los Angeles as a messenger is randomly discovered and fashioned into a pop music star.

Carry On at Your Convenience

Carry On at Your Convenience

At WC Boggs' Lavatory factory, Vic Spanner is the union representative who calls a strike at the drop of a hat. However, eventually everyone gets fed up with him.

Killikurushiyile Kudumba Mela

Killikurushiyile Kudumba Mela

A Hindu man falls in love with a Christian woman. He and his friend devises plans to introduce their romantic lives in front of parents while avoiding problems

Premaku Velayera

Premaku Velayera

A young man plans to climb the ladder of success by trying to woo his rich uncle's daughter.

Valley Girl

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 friends.

After Everything

After Everything

Besieged by writer’s block and the crushing breakup with Tessa, Hardin travels to Portugal in search of a woman he wronged in the past – and to find himself. Hoping to win back Tessa, he realizes he needs to change his ways before he can make the ultimate commitment.

Trio

Trio

When a polyamorous trio seems to be living its peaceful everyday life, the arrival of a girl is ready to upset their balance and change their destinies forever.

Private School

Private School

Private-school student Christine loves Jim. But her classmate, Jordan, is also vying for Jim's attention and trying to end his relationship with Christine. Meanwhile, Jim's friend Bubba embarks on a series of sexual escapades, including dressing up as a woman to access the girls' locker room. Despite Jim and Christine's efforts to spend some time alone, various shenanigans and schemes interfere.

The Hangover

The Hangover

When three friends finally come to after a raucous night of bachelor-party revelry, they find a baby in the closet and a tiger in the bathroom. But they can't seem to locate their best friend, Doug – who's supposed to be tying the knot. Launching a frantic search for Doug, the trio perseveres through a nasty hangover to try to make it to the church on time.

Head in the Clouds

Head in the Clouds

Gilda Bessé shares her Paris apartment with an Irish schoolteacher, Guy Malyon, and Mia, a refugee from Spain. As the world drifts toward war, Gilda defiantly pursues her hedonistic lifestyle and her burgeoning career as a photographer. But Guy and Mia feel impelled to join the fight against fascism, and the three friends are separated.

Among Ravens

Among Ravens

The story of a group of friends who reunite for their annual 4th of July weekend only to be confronted by Chad, a strange and beautiful nature photographer who begins to change their lives one by one.

The Womenists

The Womenists

Two misguided young women become feminists in order to impress a man, while rival student organizations attempt to stop their movement, threatening their future and the state of their friendship.

Utopia

Utopia

When two boys from different social backgrounds connect via the internet, they go on an adventure into the suburbs around Paris. Lost among architectural projects from times when the future was still bright, they nourish their own personal utopia.

Sofia

Sofia

While unpacking boxes in her childhood home, Sofia comes across an old camcorder. As she watches the tapes, the shaky footage awakens fragments of a past she thought was buried. The voices, laughter, and captured silences become the thread of a memory she tries to piece back together — or perhaps to rewrite.

Jaan Tere Naam

Jaan Tere Naam

Lovely Pinky Malhotra is a heart-breaker in the college where she studies, and has a number of young men who would lay down their lives for her. Amongst them are Sunil and Vicky. She is attracted to Sunil, and both carry on a romantic relationship, hoping to get married after finishing college. Before that could happen, Pinky finds out that Sunil has been two-timing her as he is already dating another young collegian. Angered and hurt at this, she decides she will have nothing to do with him, and starts her romance with Vicky. Sunil, who does not know what has transpired, wants to talk to Pinky with a view of rekindling their romance, but Pinky refuses to speak with him. The question remains is Sunil really in love with another girl, and if so, why did he take the trouble to woo Pinky?

When I Come Around

When I Come Around

Billy and Carly, two companions who must plot a course through their communication hardships, physical barriers and their individual brains to embrace in their own emotions without compromising on themselves.

Recommended Movies

Voicemails for Isabelle

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.

¿Quieres ser mi hijo?

¿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.

Someone Like You...

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.

Someone Great

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.

Players

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.

Picture This

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.

Cousins

Cousins

When Larry and Maria learn that their respective spouses are cheating on them, they try to turn the tables on them by pretending to have an affair. However, they soon find themselves falling in love.

My Sassy Girl

My Sassy Girl

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

Starting Over

Starting Over

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

The List

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.

Puppy Love

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.

About Last Night

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.

The Ugly Truth

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.

Sex Appeal

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.

Girl on a Bicycle

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 woman on a bicycle the very next day turns Paolo's life upside down.

That Awkward Moment

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 welcome him back into their circle. The three young men make a pact to have fun and avoid commitment. However, when all three find themselves involved in serious relationships, they must keep their romances secret from one another.

How to Be Single

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 filled with ever-evolving definitions of love.

Splendor

Splendor

Veronica is a white-bread beauty searching for a good man in Los Angeles. While slam dancing at a Halloween rave, she meets Abel, a sensitive poet. Then she meets Zed, a supersexy tattooed drummer with incredible biceps. Who will she choose? Does she go for true love or cheap sex? She can't decide so she chooses both. But after managing to nurture a picture-perfect threesome, along comes Ernest, a rich movie director with deep baby blues that sweep Veronica off her feet. What's a girl to do now?

Secret Admirer

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.

How I Got Into College

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.