Films like Tootsie

10 to watch next

1. 1

   Romance & Cigarettes

   Film · 2006 · also comedy and romance

   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 h...

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2. 2

   Someone Great

   Film · 2019 · also comedy and romance

   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 hear...

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3. 3

   Down with Love

   Film · 2003 · also comedy and romance

   In 1962 New York City, love blossoms between a playboy journalist and a feminist advice author.

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4. 4

   Someone Like You...

   Film · 2001 · also comedy and romance

   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 wh...

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5. 5

   How to Be Single

   Film · 2016 · also comedy and romance

   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 i...

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6. 6

   Ricky Stanicky

   Film · 2024 · also comedy

   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 th...

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7. 7

   The Lonely Guy

   Film · 1984 · also comedy and romance

   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.

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8. 8

   One Night Only

   Film · 2026 · also comedy and romance

   Two love-starved strangers crash into each other on the one night of the year when single people are allowed to have sex.

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9. 9

   She's Gotta Have It

   Film · 1986 · also comedy and romance

   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 c...

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10. 10

    Sleeping with Other People

    Film · 2015 · also comedy and romance

    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 e...

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