
Playing It Cool
A young man meets and instantly falls in love with an engaged woman.
Movies Like Playing It Cool
Similar in style, tone, and themes — find your next watch.

¿Quieres ser mi hijo?
2023★ 8.5
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...
2001★ 6.0
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
2019★ 6.4
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.

How to Date Billy Walsh
2024★ 6.4
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.

Players
2024★ 6.1
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.

Dinner in America
2020★ 7.7
An on-the-lam punk rocker and a young woman obsessed with a local band go on an unexpected and epic journey together through the decaying suburbs of the American Midwest.

Picture This
2025★ 6.0
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.

Sex Appeal
2022★ 6.6
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.

My Sassy Girl
2008★ 6.8
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.

About Last Night
2014★ 6.0
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.

French Girl
2024★ 6.3
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.

The List
2023★ 5.9
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.

Desperados
2020★ 6.0
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.

Starting Over
1979★ 6.4
After divorcing his ambitious singer wife, a middle-aged man begins a new relationship with a teacher.

10
1979★ 5.8
A Hollywood songwriter goes through a mid-life crisis and becomes infatuated with a sexy blonde newlywed.

Cousins
1989★ 6.0
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.

No Hard Feelings
2023★ 6.7
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.

Puppy Love
2023★ 7.0
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.

Bros
2022★ 6.6
Two gay men are possibly, probably, stumbling towards love. Maybe. They're both very busy.

The Ugly Truth
2009★ 6.5
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.