Most Similar Movies to Playing It Cool (2014)


If you are looking for movies like Playing It Cool (2014), you might like movies tagged with keyword : romance, comedy, love, screenwriter, writer, hollywood, contemporary, urban, emotion, dating, relationship, humor, satire, coming of age, self-discovery, dilemma, challenge, transformation, life, choice .


Then Came You (2018), What If (2013), Only You (2018), Love & Other Drugs (2010), Casomai (2002), In the Land of Women (2007), The Good Guy (2009) ... Let's take a look at the following list...

Then Came You (2018)

Then Came You (2018)

7.0/10 Romance, Comedy, Drama

A hypochondriac working as an airport baggage handler is forced to confront his fears when a British teenager with a terminal illness enlists him to help her carry out her eccentric bucket list.

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What If (2013)

What If (2013)

7.4/10 Romance

A medical-school dropout (Daniel Radcliffe) tries to hide his attraction to his new friend (Zoe Kazan), a bubbly artist who already has a boyfriend.

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Only You (2018)

Only You (2018)

6.8/10 Drama, Romance

Elena and Jake meet by chance on New Years Eve, arguing for the same taxi. However, instead of going their separate ways after sharing a taxi ,they start a passionate relationship.

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Love & Other Drugs (2010)

Love & Other Drugs (2010)

6.7/10 Comedy, Drama, Romance

A young woman suffering from Parkinson's befriends a drug rep working for Pfizer in 1990s Pittsburgh.

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Casomai (2002)

Casomai (2002)

6.5/10 Comedy, Romance, Drama

Stefania and Tommaso are to marry and want their wedding to be special. They travel to Stefania's childhood church and there meet a priest who rises to the challenge. In the ceremony the couple are confronted with not only the beauty of their love but also the darker challenges of marriage; the loss of togetherness, the temptations, the interference of others. Yet, th...Read all

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In the Land of Women (2007)

In the Land of Women (2007)

6.4/10 Comedy, Drama, Romance

A sleazy writer has a chance to redeem himself when he goes to stay with his grandmother and befriends the neighbors.

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The Good Guy (2009)

The Good Guy (2009)

5.8/10 Comedy, Romance, Drama

Calm and quiet Daniel starts on Wall Street. His womanizing colleague, Tommy, encourages him to meet women. He unknowingly meets Tommy's girlfriend, Beth, and ends up in her 5 women book club. Will he find the woman?

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Silver Linings Playbook (2012)

Silver Linings Playbook (2012)

7.7/10 Comedy, Romance, Drama

After a stint in a mental institution, former teacher Pat Solitano moves back in with his parents and tries to reconcile with his ex-wife. Things get more challenging when Pat meets Tiffany, a mysterious girl with problems of her own.

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You Can't Say No (2018)

You Can't Say No (2018)

4.0/10 Comedy

Just days from signing divorce papers, Hank and Alexandra give their relationship one final shot by playing a game with only one rule: no matter what they ask each other to do, they can't say no.

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Checking Out (2005)

Checking Out (2005)

3.8/10 Comedy

On the eve of his 90th birthday, a retired actor (Peter Falk) tells his three children (Laura San Giacomo, Judge Reinhold) that he plans to kill himself.

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Almost Love (2019)

Almost Love (2019)

6.7/10 Gay & Lesbian, Romance

A couple are about to find out if their relationship has an expiration date.

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Play the Game (2008)

Play the Game (2008)

6.4/10 Romance, Comedy

A young ladies' man teaches his dating tricks to his lonely, widowed grandfather, and plays his best mind games to meet the woman of his dreams.

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Rainbow Time (2016)

Rainbow Time (2016)

5.9/10 Comedy, Drama

A developmentally delayed 40 year old man named Shonzi is sent to live with his brother Todd. But when Shonzi develops a crush on Todd's girlfriend Lindsay, he threatens to reveal past secrets that could ultimately tear the couple apart.

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Late Bloomers (2011)

Late Bloomers (2011)

5.7/10 Comedy, Romance, Drama

The struggles of Mary and her husband adjusting to retirement.

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(500) Days of Summer (2009)

(500) Days of Summer (2009)

8.5/10 Romance, Comedy, Drama

After his girlfriend (Zooey Deschanel) dumps him, a greeting-card writer (Joseph Gordon-Levitt) reflects on their 500 days together to try to figure out where their love affair went wrong.

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Funny Story (2018)

Funny Story (2018)

5.1/10 Comedy, Drama, Gay & Lesbian

A dramedy about a well-intentioned father who inadvertently wreaks havoc on the life of his estranged daughter when she invites him to her woodland wedding.

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Sister of the Groom (2020)

Sister of the Groom (2020)

4.7/10 Romance, Comedy, Drama

On Audrey's 40th birthday, her brother is marrying a girl he met in France. Secrets are revealed prior to the wedding. Audrey and the young, French fiancee do NOT get along.

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Kabhi Haan Kabhi Naa (1994)

Kabhi Haan Kabhi Naa (1994)

7.8/10 Comedy, Drama, Music, Musical

Sunil and some of his friends start a band and perform at weddings and special occasions. Sunil is in love with Aana but Aana loves Chris; when Sunil finds out about this he decides to ...

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