20 best movies like Playing It Cool (2014)

When a chance encounter brings together the cynical Dell and the quick-witted Kimberly, the stage is set for a tempestuous love affair that unfolds like a puzzle. As the film zigzags back and forth in time-from a meteor shower in LA, to an encounter in a Paris hotel room, to a fateful phone call-an unforgettable portrait of a relationship emerges.

The film tells the story of quick-witted teen Mark, contentedly living the same day in an endless loop whose world is turned upside-down when he meets mysterious Margaret also stuck in the time loop. Mark and Margaret form a magnetic partnership, setting out to find all the tiny things that make that one day perfect. What follows is a love story with a fantastical twist, as the two struggle to figure out how -- and whether -- to escape their never-ending day.

When college friends reunite after 15 years over the Christmas holidays, they discover just how easy it is for long-forgotten rivalries and romances to be reignited.

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

Former childhood pals Leo and Nikki are attracted to each other as adults—but will their feuding parents' rival pizzerias put a chill on their sizzling romance?

Three World War II buddies promise to meet at a specified place and time 10 years after the war. They keep their word only to discover how far apart they've grown. But the reunion sparks memories of youthful dreams that haven't been fulfilled -- and slowly, the three men reevaluate their lives and try to find a way to renew their friendship.

A broken family finds their relationships to one another changed by a new arrival in the household.

In an updated contemporary version of the beloved stage play and 1989 film, "Steel Magnolias" chronicles the lives and friendship of six women in Louisiana. Supporting each other through their triumphs and tragedies, they congregate at Truvy’s beauty shop to ponder the mysteries of life and death, husbands and children - and hair and nails - all the important topics that truly unite and celebrate women.

Iris invites her friend Jack to stay at her family's island getaway after the death of his brother. At their remote cabin, Jack's drunken encounter with Hannah, Iris' sister, kicks off a revealing stretch of days.

Miranda Presley moves from New York to Nashville to become a songwriter. At an unsuccessful audition she meets James Wright, a promising newcomer. After only a few days they marry but start to quickly regret it.

Narcissistic, brash, and self-destructive Jimmy thinks all relationships are doomed. Cynical, people-pleasing, and stubborn Gretchen knows that relationships aren't for her. So when they meet at a wedding, it's only natural that the two of them go home together and, despite their better judgment, begin to find themselves falling for each other.

A 29-year-old lawyer and her lesbian best friend experience a dramatic shift in their longtime bond after one enters a serious relationship

Can two serial cheaters get a second chance at love? After a one-night stand in college, New Yorkers Lainey and Jake meet by chance twelve years later and discover they each have the same problem: because of their monogamy-challenged ways, neither can maintain a relationship. Determined to stay friends despite their mutual attraction, they make a pact to keep it platonic, a deal that proves easier said than done.

After her mother's death, mediocre chef Amanda Shelton is having trouble attracting customers to her family's restaurant. While shopping for ingredients, she is given a magical crab by mysterious Gene O'Reilly. Afterward, Amanda's dishes suddenly become excellent, inducing strong emotional reactions in everyone who eats them. Tom Bartlett, who is preparing to open his own eatery, tries her cooking and falls in love.

Jodi, the tallest girl in her high school, has always felt uncomfortable in her own skin. But after years of slouching, being made fun of, and avoiding attention at all costs, Jodi finally decides to find the confidence to stand tall.

Dave, a high school senior, spends most of his time pining away over a girl he can’t have. Aubrey, a junior with artistic aspirations, has a hot boyfriend who doesn’t quite understand her or seem to care. Although they go to different schools, Dave and Aubrey find themselves at the same party. When both head outside to get some air, they meet. A casual conversation sparks an instant connection, and, over the course of a weekend, things turn magical, romantic, complicated, and funny as Aubrey and Dave discover what it's like to fall in love for the first time.

Rebellious Mickey and good-natured Gus navigate the thrills and agonies of modern relationships.

As her marriage dissolves, a Manhattan writer takes driving lessons from a Sikh instructor with marriage troubles of his own. In each other's company they find the courage to get back on the road and the strength to take the wheel.

A family dog—with a near-human soul and a philosopher's mind—evaluates his life through the lessons learned by his human owner, a race-car driver.

A widow falls for a guy who bears a striking resemblance to her late husband.

Xavier is a 40-year-old father of two who still finds life very complicated. When the mother of his children moves to New York, he can't bear them growing up far away from him and so he decides to move there as well.

An unusual, real-world romance involving relatable people, with one catch - there are three of them! You Me Her infuses the sensibilities of a smart, grounded indie rom-com with a distinctive twist: one of the two parties just happens to be a suburban married couple.

Victor Bukowski is an out-of-work actor with problems. He's got a lousy agent, he has a habit of falling out with directors and he's still in love with his ex-girlfriend. However, Victor is about to embark on an unexpected emotional journey which will make him confront his future and his past mistakes.

In New York, a struggling actress and a successful writer sing about their failed marriage from two perspectives.

A young woman struggles to move on with her life after the death of her husband, an acclaimed folk singer, when a brash New York writer forces her to confront her loss and the ambiguous circumstances of his death.

Soon-to-be-wed graduate student Finn Dodd develops cold feet when she suspects her fiancé is cheating on her. In order to clear her head, Finn visits her grandmother, Hy, and great aunt, Glady Joe Cleary, in Grasse, Calif. There, Finn learns that Hy and Glady Joe are members of a group of passionate quilters, and over the course of her visit she is regaled with tales of love and life by women who have collected rich experiences and much wisdom.

The story of a young man who arrives in Hollywood during the 1930s hoping to work in the film industry, falls in love, and finds himself swept up in the vibrant café society that defined the spirit of the age.

As a young New York couple goes from college romance to marriage and the birth of their first child, the unexpected twists of their journey create reverberations that echo over continents and through lifetimes.

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?

Billy, a struggling young gay photographer (who likes Polaroids), tired of being the "other man", falls in love with Gabriel, a waiter and aspiring musician who is probably straight but possibly gay or at least curious. Billy tries to get Gabriel to model for his latest project, a series of remakes of famous Hollywood screen kisses, featuring male couples, while also trying to win his affections.

When the fleet puts in at San Francisco, sailor Bake Baker tries to rekindle the flame with his old dancing partner, Sherry Martin, while Bake's buddy Bilge Smith romances Sherry's sister, Connie. But it's not all smooth sailing—Bake has a habit of losing Sherry's jobs for her and, despite Connie's dreams, Bilge is not ready to settle down.

A young writer begins an affair with an older woman from France whose open marriage to a diplomat dictates that they can meet only between the hours of 5 p.m. to 7 p.m.

During their travels from Chicago to New York, Harry and Sally Will debate whether or not sex ruins a perfect relationship between a man and a woman. Eleven years later, and they're still no closer to finding the answer.

Overachieving actress, Rebecca (Moore), must come to grips with her failing marriage to stay-at-home dad, Tom (Duchovny). While Rebecca's slacker brother, Tobey (Billy Crudup), can't seem to commit to his aspiring-novelist girlfriend, Elaine (Maggie Gyllenhaal). As both relationships spin out of control, the two couples embark on a quest to rediscover the magic and romance of falling in love in New York.

When Johnny is released from prison following a forgery charge, he quickly lands a job as a short-order cook at a New York diner. Following a brief fling with waitress Cora, Frankie develops an attraction for Cora's friend and fellow waitress Frankie. While Frankie resists Johnny's charms initially, she eventually relents when her best friend, Tim, persuades her to give Johnny a chance.

When unsuccessful actress Clarissa returns to her hometown for a wedding and tries to impress her old friends by claiming she's dating big time celebrity Chas Hunter, she suddenly finds herself in a comically false engagement when her lies go public and Chas decides to join the festivities in a stunt to escape bad press.

After spending eight months in a mental institution, a former teacher moves back in with his parents and tries to reconcile with his ex-wife.

Inspired by a true story, a comedy centered on a 27-year-old guy who learns of his cancer diagnosis, and his subsequent struggle to beat the disease.

Eugene and Rick are two struggling artists who share apartment. However, Rick has problems with that, because Eugene is obsessed with pulp fiction comic books and has nightmares because of that. Rick soon finds that those nightmares could be excellent material for writing his own comic books.

Jenny Farrell is getting married. But how will her straight-laced family react when they find out that the woman they thought was their daughter’s roommate is actually her fiancée? As the old-fashioned Farrells attempt to come to terms with the prospect of a surprise daughter-in-law, they face a difficult choice: either adapt with the times or risk being left behind.

Patrick returns to San Francisco for the first time in almost a year to celebrate a momentous event with his old friends. In the process, he must face the unresolved relationships he left behind and make difficult choices about what’s important to him.

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.

When a hapless but dedicated talent manager signs his first client who actually has talent, his career finally starts to take off.

A sudden loss disrupts Carol’s orderly life, propelling her into the dating world for the first time in 20 years. Finally living in the present tense, she finds herself swept up in not one, but two unexpected relationships that challenge her assumptions about what it means to grow old.

With a new iPhone, an apartment near the Grove, and a comfortable bank account left to her by her beloved late husband, Marnie Minervini has happily relocated from New Jersey to Los Angeles to be near her daughter Lori, a successful (but still single) screenwriter, and smother her with motherly love. But when the dozens of texts, unexpected visits, and conversations dominated by unsolicited advice force Lori to draw strict personal boundaries, Marnie finds ways to channel her eternal optimism and forceful generosity to change the lives of others - as well as her own - and find a new purpose in life.

In 1850 Oregon, when a backwoodsman brings a wife home to his farm, his six brothers decide that they want to get married too.

Lovely Linda Mason has crooner Jim Hardy head over heels, but suave stepper Ted Hanover wants her for his new dance partner after femme fatale Lila Dixon gives him the brush. Jim's supper club—Holiday Inn—is the setting for the chase by Hanover and manager Danny Reed. The music's the thing.

At a picturesque lakeside estate, a love triangle unfolds between the legendary diva Irina, her lover Boris, and the ingénue Nina.

Amy, a naive college graduate who believes she's destined to be a great poet, begrudgingly accepts a job at a sex shop while she pursues a mentorship with reclusive writer Rat Billings.

Morgan is the inspiring story of Morgan Oliver, a gay young athlete determined that a bicycle accident that left him paralyzed will not change him. He takes a chance on love when he meets Dean Kagen on a basketball court. Dean helps Morgan train for the same race in which he had his accident. But when he sees that Morgan will risk everything to win, Dean walks out. Left alone to face the race and demons that caused his accident, Morgan teeters between what he needs and what he wants. Can he find the strength to pull himself back up again?