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Movies Like I Probably Shouldn't Be Telling You This

If you liked I Probably Shouldn't Be Telling You This (2023), a drama movie directed by Emma Weinswig, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

  1. 1What Maisie Knew

    What Maisie Knew (2013)

    ★ 7.1/10Also drama

    In New York City, six-year-old Maisie is caught in the middle of a bitter custody battle between her self-absorbed parents—an aging rock singer mother and a distracted art dealer father. As both quickly marry new…

  2. 2Hungry Hearts

    Hungry Hearts (2015)

    ★ 6.5/10Also drama

    The relationship of a couple who meet by chance in New York City is put to the test when they encounter a life or death circumstance.

  3. 3Rogue Agent

    Rogue Agent (2022)

    ★ 6.3/10Also drama

    Conman Robert Freegard poses as an undercover MI5 agent and kidnaps countless victims amidst a high-stakes manhunt, until the woman who fell for him brings him to justice.

  4. 4Fast Girls

    Fast Girls (2012)

    ★ 6/10Also drama

    A street smart runner develops an intense rivalry with an equally ambitious wealthy young athlete.

  5. 5Hardball

    Hardball (2001)

    ★ 6.5/10Also drama

    An aimless young man who is scalping tickets, gambling and drinking, agrees to coach a Little League team from the Cabrini Green housing project in Chicago as a condition of getting a loan from a friend.

  6. 6The Young One

    The Young One (1960)

    ★ 7/10Also drama

    A jazz musician seeks refuge from a lynch mob on a remote island, where he meets a hostile game warden and the young object of his attentions.

  7. 7Charm City Kings

    Charm City Kings (2020)

    ★ 7.8/10Also drama

    Mouse desperately wants to join The Midnight Clique, the infamous Baltimore dirt bike riders who rule the summertime streets. When Midnight’s leader, Blax, takes 14-year-old Mouse under his wing, Mouse soon finds…

  8. 8The Sound of Silence

    The Sound of Silence (2019)

    ★ 5.9/10Also drama

    A successful "house tuner" in New York City, who calibrates the sound in people's homes in order to adjust their moods, meets a client with a problem he can't solve.

  9. 9Pimp

    Pimp (2018)

    ★ 6.2/10Also drama

    An urban love story set on the hard streets of the Bronx. A struggling female pimp, named Wednesday, grows up learning the game from her dad. Once he's gone she's left to look out for her prostitute mother and…

  10. 10O.G.

    O.G. (2018)

    ★ 5.9/10Also drama

    Louis Menkins is five weeks away from being released after 26 years in prison. He is faced with the decision to put his own release at risk in order to protect a young man named Beecher from growing gang controversies.

  11. 11Hello

    Hello (2022)

    ★ 6.3/10Also drama

    An emotionally unavailable flight attendant meets a potential love interest and later finds out that her "perfect guy" has ulterior motives. As the clock ticks down on New Year's Eve, she must fight to keep her…

  12. 12The Good Neighbor

    The Good Neighbor (2022)

    ★ 6.7/10Also drama

    A nightmarish evening unfolds for neighbors David and Robert when they accidentally hit a woman on her bike and flee the scene. While David is increasingly plagued by feelings of guilt, Robert shows no remorse and…

  13. 13Girl in the Box

    Girl in the Box (2016)

    ★ 6.7/10Also drama

    The true story of 20-year-old Colleen Stan, a hitchhiking woman abducted by a young couple and held captive for seven years, during which time she's tortured and forced to live as a slave to her captors.

  14. 14Eleanor the Great

    Eleanor the Great (2025)

    ★ 6.8/10Also drama

    94-year-old Eleanor Morgenstein tries to rebuild her life after the death of her best friend. As a result, she moves back to New York City after living in Florida for decades.

  15. 15F.I.S.T.

    F.I.S.T. (1978)

    ★ 6.5/10Also drama

    Johnny Kovak joins the Teamsters trade-union in a local chapter in the 1930s and works his way up in the organization. As he climbs higher and higher his methods become more ruthless and finally senator Madison starts…

  16. 16Gracie

    Gracie (2007)

    ★ 6.2/10Also drama

    A teenager faces an uphill battle when she fights to give women the opportunity to play competitive soccer.

  17. 17The House on Carroll Street

    The House on Carroll Street (1988)

    ★ 5.9/10Also drama

    A reporter, fired after refusing to give names to a 1951 House Un-American Activities Committee, takes a part-time job as companion to an old lady. While working she overhears a noisy argument in the neighboring house…

  18. 18Hands of Stone

    Hands of Stone (2016)

    ★ 6.6/10Also drama

    The legendary Roberto Duran and his equally legendary trainer Ray Arcel change each other's lives.

  19. 19Salomé

    Salomé (2013)

    ★ 6.1/10Also drama

    After the lewd and frenetic Dance of the Seven Veils, and with the solemn pledge from the very lips of Herod himself that she could have whatever her heart desires up to half his kingdom, wanton and proud young Salomé…

  20. 20Cardboard Boxer

    Cardboard Boxer (2016)

    ★ 6.5/10Also drama

    Gentle and broken, a homeless man fights others on video for money but soon finds comfort in an unlikely friend and the lost diary of a young girl.

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