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Movies Like How to Please a Woman

Find movies like How to Please a Woman using TMDB similarity plus Movie Rankings community context. Our top current pick is Sitting in Bars with Cake. Browse 18 related titles with direct links to rankings, cast pages, and matchup data.

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Recommended If You Liked How to Please a Woman
TMDB Recommended

Sitting in Bars with Cake

2023

Extrovert Corinne convinces Jane, a shy, talented baker, to commit to a year of bringing cakes to bars, to help her meet people and build confidence. But when Corinne receives a life-altering diagnosis, the pair faces a challenge unlike anything they've experienced before.

TMDB Recommended

The Best You Can

2025

Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, just as her world is turned upside down by the arrival of sharp but chronically underachieving security guard Stan Olszewski in this smart rom-com that reunites Bacon and Sedgwick on screen for the first time in 20 years.

TMDB Recommended

Mumford

1999

When a would-be psychologist, curiously named Dr. Mumford, comes to the idyllic town of the same name and offers his talent for listening and a disarming frankness, the town's quirkiest citizens scramble for a seat on his couch. As he lightens hearts darkened by old secrets no one realizes he's hiding a whopper of his own, or that he's fallen head over heels for one of his patients!

TMDB Recommended

(Untitled)

2009

A fashionable contemporary art gallerist in Chelsea, New York falls for a brooding new music composer in this comic satire of the state of contemporary art.

TMDB Recommended

Dirty Sexy Saint

2019

Clay Kincaid hates the nickname 'Saint', he got for being too kind to stray animals and desperate people. Especially when it comes to women. With a rough and damaged past that has left him jaded, he doesn't do committed relationships. This is before he meets Samantha Jamieson, an heiress turned runaway in need of help. When she starts to work as a waitress at his bar, he discovers that she is someone truly special and amazing… someone that could warm his damaged heart.

TMDB Recommended

Enemies, a Love Story

1989

A ghostwriter finds himself romantically involved with his current wife, a married woman and his long-vanished wife.

TMDB Recommended

Night Owls

2015

After workaholic Kevin has a drunken one night stand with the beautiful train-wreck Madeline, he's horrified to discover that she's actually his boss' jilted ex-mistress. When she takes a bottle of sleeping pills, Kevin is forced to keep her awake... and over the course of the night the two begin to fall for each other.

TMDB Recommended

The Good House

2021

Hildy Good, a wry New England realtor and descendant of the Salem witches who loves her wine and loves her secrets. Her compartmentalized life starts to unravel as she rekindles an old romance and becomes dangerously entwined in one person’s reckless behavior.

TMDB Recommended

Love & Sex

2000

When her rather explicit copy is rejected, magazine journalist Kate is asked by her editor to come up with an article on loving relationships instead, and to do so by the end of the day. This gets Kate thinking back over her own various experiences, and to wondering if she is in much of a position to write on the subject.

TMDB Recommended

Cosi

1996

Lewis, a young amateur theater director, is offered a job with a governmental program for the rehabilitation of mentally ill patients in a Sydney institution. His project is overrun by one of the patients, who wants to stage the opera Cosi Fan Tutte by Mozart, despite the fact that none of the patients can sing or speak Italian. A comedy of errors ensues, but one which unifies the patients and their director in unexpected ways.

TMDB Recommended

Strictly Sexual

2008

Two successful women, sick and tired of dating and relationships, decide to keep two young men in their pool house for strictly sexual purposes.

TMDB Recommended

Extracurricular Activities

2019

The outrageous life of Reagan Collins, a model high school student with a "killer" after-school job that involves arranging “accidents” for his classmates' parents. When seasoned police detective Cliff Dawkins starts putting the pieces together, it's a battle of wits to see if Reagan can keep business booming.

TMDB Recommended

Jack Goes Boating

2010

A limo driver's blind date sparks a tale of love, betrayal, friendship and grace—centered on two working-class New York City couples.

TMDB Recommended

Breaking & Exiting

2018

Harry, a charming house thief, gets more than he bargains for during an attempted burglary when he stumbles upon Daisy and decides to save her from herself, sending both of them into a darkly comedic journey of self discovery and love.

TMDB Recommended

The Elder Son

2006

A thief on the run convinces a single father that he is his long-lost son. Complications ensue when he falls in love with his newfound "sister".

TMDB Recommended

Cyrus

2010

With John's social life at a standstill and his ex-wife about to get remarried, a down on his luck divorcée finally meets the woman of his dreams, only to discover she has another man in her life - her son. Before long, the two are locked in a battle of wits for the woman they both love-and it appears only one man can be left standing when it's over.

TMDB Recommended

XX/XY

2002

Three friends begin a dangerous three-way relationship that spirals out of control, leading to dire consequences that haunt them ten years later.

TMDB Recommended

Greenberg

2010

Roger Greenberg, a failed musician now making a living as a carpenter in New York, returns to Los Angeles to house-sit for his brother. He's stranded there—since he doesn't drive—until his brother's assistant, Florence, comes to his rescue. She's as much a lost soul as he is, and the pair form a significant connection—giving Roger a much-needed reason to be happy.

What are the best movies like How to Please a Woman?

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