
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.

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.

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.

The Moment
2026★ 6.3
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.

¿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.

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

Focus
2015★ 6.9
Nicky, an accomplished con artist, gets romantically involved with his disciple Jess but later ends their relationship. Years later, she returns as a femme fatale to spoil his plans.

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.

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.

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.

Just One of the Guys
1985★ 6.4
When Terry Griffith loses her high school's writing competition, she's convinced that it's because she's a girl. So Terry decides to change high schools and pose as a boy to prove her point. Her brother, Buddy, helps her pass as a guy so well that she is soon making friends with the boys at school, including the attractive Rick, who becomes her new best friend. But her gender-swapping makes things difficult when she falls in love with him.

The Rebound
2009★ 6.5
Upon discovering her husband's infidelity, Sandy leaves the suburbs and moves into the city. There, she befriends Aram, a guy whose wife only married him so she could get a green card. Sandy hires Aram to be her nanny, and it isn't long until Aram and Sandy find out they get along wonderfully and start to date. But is their relationship real or is it, in fact, just a rebound for both of them?