
Tootsie
When struggling, out of work actor Michael Dorsey secretly adopts a female alter ego—Dorothy Michaels—in order to land a part in a daytime drama, he unwittingly becomes a feminist icon and ends up in a romantic pickle.
Movies Like Tootsie
Similar in style, tone, and themes — find your next watch.

Romance & Cigarettes
2005★ 6.0
Ironworker Nick lives with his wife, Kitty, and three daughters. When he meets a significantly younger woman, Tula, he starts an affair with her, much to the chagrin of his wife, and his life is thrown into upheaval. Kitty kicks Nick out of the house, and he is forced to make some difficult decisions.

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.

Down with Love
2003★ 6.1
In 1962 New York City, love blossoms between a playboy journalist and a feminist advice author.

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.

How to Be Single
2016★ 6.3
New York City is full of lonely hearts seeking the right match, and what Alice, Robin, Lucy, Meg, Tom and David all have in common is the need to learn how to be single in a world filled with ever-evolving definitions of love.

Ricky Stanicky
2024★ 6.5
When three childhood best friends pull a prank gone wrong, they invent the imaginary Ricky Stanicky to get them out of trouble. Twenty years later, the trio still uses the nonexistent Ricky as a handy alibi for their immature behavior. But when their spouses and partners get suspicious and demand to finally meet the fabled Mr. Stanicky, the guilty trio decide to hire a washed-up actor and raunchy celebrity impersonator to bring him to life.

She's Gotta Have It
1986★ 6.6
The story of Nola Darling's simultaneous sexual relationships with three different men is told by her and by her partners and other friends. All three men wanted her to commit solely to them; Nola resists being "owned" by a single partner.

Sleeping with Other People
2015★ 6.3
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.

Friends with Benefits
2011★ 6.6
Dylan is done with relationships. Jamie decides to stop buying into the Hollywood clichés of true love. When the two become friends they decide to try something new and take advantage of their mutual attraction - but without any emotional attachment.

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.

The Lonely Guy
1984★ 6.2
A writer for a greeting card company learns the true meaning of loneliness when he comes home to find his girlfriend in bed with another man.

The Moment
2026★ 6.4
A rising pop sensation navigates fame and industry pressures while preparing for her arena tour debut, revealing the transformation of underground culture into mainstream success.

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.

The Seven Year Itch
1955★ 7.0
When his family goes away for summer vacation, a hitherto faithful publishing executive with an overactive imagination is tempted by an attractive new neighbor.

My Fake Boyfriend
2022★ 5.9
A young man in a tricky situation follows the advice of his unconventional best friend and uses social media to create a fake boyfriend to keep his awful ex-lover out of his life. But everything backfires when he meets the real love of his life, and breaking up with his fake boyfriend proves hard to do.

What's New Pussycat?
1965★ 6.0
A playboy who refuses to give up his hedonistic lifestyle to settle down and marry his true love seeks help from a demented psychoanalyst who is having romantic problems of his own.

Can't Hardly Wait
1998★ 6.2
It's graduation day at Huntington Hills High, and you know what that means - time to party. And not just any party, either. This one will be a night to remember, as the nerds become studs, the jocks are humiliated, and freshman crushes blossom into grown-up romance.

¿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.

Fading Gigolo
2013★ 5.8
Fioravante decides to become a professional Don Juan as a way of making money to help his cash-strapped friend, Murray. With Murray acting as his "manager", the duo quickly finds themselves caught up in the crosscurrents of love and money.

Broadcast News
1987★ 6.8
A high-strung news producer finds herself in a love triangle between a talented but self-doubting reporter and a charming news anchor who embodies the growing trivialization of news that she is determined to fight against.