Best movies like Playing It Cool

Similar in 83%

Lust for Love (2014)

Plot Summary:

Winning your childhood sweetheart can create more problems than it solves.

Similar in 75%

I Want You Back (2022)

Plot Summary:

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.

Similar in 85%

A Christmas Kiss (2011)

Plot Summary:

Wendy Walton is the best designer in Boston... but no one knows it yet. Hoping to kick-start her career, Wendy has left work with the local theatre to take a job as an assistant to Priscilla Hall, the most prestigious designer in the city. Ms. Hall works Wendy around the clock, which is how Wendy finds herself trapped in an elevator late one night with an incredibly handsome stranger. Wendy and the mystery man share an impulsive, romantic, life changing kiss before the doors open and Wendy runs out, leaving him behind. The next day at work, Wendy answers the door to find the handsome gentleman standing in front of her.

Similar in 76%

Bride Wars (2009)

Plot Summary:

Two best friends become rivals when their respective weddings are accidentally booked for the same day.

Similar in 86%

The Rebound (2009)

Plot Summary:

Sandy, upon discovering her husband's infidelity while watching her son's birthday video, leaves the suburbs and moves into the city. She gets an apartment that's above a coffee house where she befriends one of the workers, Aram, a guy whose wife only married him so she could get a green card. Aram's family thinks he's wasting his life and education by working in the coffee house. Soon after moving into the apartment, Sandy hires Aram to be her nanny while she takes on work for the first time since her children where born. It isn't long when Aram and Sandy find they get along wonderfully and start to date. But the question is: is their relationship real or is it, in fact, just a rebound for both of them?.

Similar in 84%

No Strings Attached (2011)

Plot Summary:

Emma is a busy doctor who sets up a seemingly perfect arrangement when she offers her best friend Adam a relationship with one rule: No strings attached. But when a fling becomes a thing, can sex friends stay best friends?.

Similar in 90%

The Wedding Planner (2001)

Plot Summary:

Mary Fiore, San Francisco's premiere wedding planner is rescued from an accident by the man of her dreams, pediatrician Steve Edison, only to find he is the fiancé of her latest client, wealthy Fran Donnolly. As Mary continues making the wedding arrangements, she and Steve are put into a string of uncomfortable situations that force them to face their mutual attraction.

Similar in 84%

What If (2013)

Plot Summary:

Wallace, a medical school dropout, has been repeatedly burned by bad relationships. So while everyone around him, including his roommate Allan, seems to be finding the perfect partner, Wallace decides to put his love life on hold. It is then that he meets Chantry, an animator who lives with her long term boyfriend Ben. Wallace and Chantry form an instant connection, striking up a close friendship. But there is no denying the chemistry between them, leading the pair to wonder: what if the love of your life is actually your best friend?.

Similar in 80%

What's Your Number? (2011)

Plot Summary:

Ally Darling (Anna Faris) is realizing she's a little lost in life. Her latest romance has just fizzled out, and she's just been fired from her marketing job. Then she reads an eye-opening magazine article that warns that 96 percent of women who've been with 20 or more lovers are unlikely to find a husband. Determined to turn her life around and prove the article wrong, Ally embarks on a mission to find the perfect mate from among her numerous ex-boyfriends.

Similar in 79%

Something Borrowed (2011)

Plot Summary:

Though Rachel (Ginnifer Goodwin) is a successful attorney and a loyal, generous friend, she is still single. After one drink too many at her 30th-birthday celebration, Rachel unexpectedly falls into bed with her longtime crush, Dex -- who happens to be engaged to her best friend, Darcy (Kate Hudson). Ramifications of the liaison threaten to destroy the women's lifelong friendship, while Ethan (John Krasinski), Rachel's confidant, harbors a potentially explosive secret of his own.

Similar in 82%

Leap Year (2010)

Plot Summary:

When yet another anniversary passes without a marriage proposal from her boyfriend, Anna decides to take action. Aware of a Celtic tradition that allows women to pop the question on Feb. 29, she plans to follow her lover to Dublin and ask him to marry her. Fate has other plans, however, and Anna winds up on the other side of the Emerald Isle with handsome, but surly, Declan -- an Irishman who may just lead Anna down the road to true love.

Similar in 82%

What Happens in Vegas (2008)

Plot Summary:

During a wild vacation in Las Vegas, career woman Joy McNally and playboy Jack Fuller come to the sober realization that they have married each other after a night of drunken abandon. They are then compelled, for legal reasons, to live life as a couple for a limited period of time. At stake is a large amount of money.

Similar in 85%

My Best Friend's Girl (2008)

Plot Summary:

When Dustin's girlfriend, Alexis, breaks up with him, he employs his best buddy, Tank, to take her out on the worst rebound date imaginable in the hopes that it will send her running back into his arms. But when Tank begins to really fall for Alexis, he finds himself in an impossible position.

Similar in 77%

This Means War (2012)

Plot Summary:

Two top CIA operatives wage an epic battle against one another after they discover they are dating the same woman.

Similar in 78%

27 Dresses (2008)

Plot Summary:

Altruistic Jane finds herself facing her worst nightmare as her younger sister announces her engagement to the man Jane secretly adores.

Similar in 86%

Just Go with It (2011)

Plot Summary:

A plastic surgeon, romancing a much younger schoolteacher, enlists his loyal assistant to pretend to be his soon to be ex-wife, in order to cover up a careless lie. When more lies backfire, the assistant's kids become involved, and everyone heads off for a weekend in Hawaii that will change all their lives.

Similar in 85%

The Perfect Date (2019)

Plot Summary:

No beau? No problem! To earn money for college, a high schooler creates a dating app that lets him act as a stand-in boyfriend.

Similar in 79%

That Awkward Moment (2014)

Plot Summary:

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.

Similar in 81%

Made of Honor (2008)

Plot Summary:

Tom and Hannah have been platonic friends for 10 years. He's a serial dater, while she wants marriage but hasn't found Mr. Right. Just as Tom is starting to think that he is relationship material after all, Hannah gets engaged. When she asks Tom to be her 'maid' of honor, he reluctantly agrees just so he can attempt to stop the wedding and woo her.

Similar in 76%

The Holiday (2006)

Plot Summary:

Two women, one (Cameron Diaz) from America and one (Kate Winslet) from Britain, swap homes at Christmastime after bad breakups with their boyfriends. Each woman finds romance with a local man (Jude Law, Jack Black) but realizes that the imminent return home may end the relationship.

Similar in 87%

Love, Rosie (2014)

Plot Summary:

Since the moment they met at age 5, Rosie and Alex have been best friends, facing the highs and lows of growing up side by side. A fleeting shared moment, one missed opportunity, and the decisions that follow send their lives in completely different directions. As each navigates the complexities of life, love, and everything in between, they always find their way back to each other - but is it just friendship, or something more? Based on Cecelia Ahern's bestselling novel, LOVE, ROSIE is a heart-warming, modern comedy-of-errors posing the ultimate question: do we really only get one shot at true love?.