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Movies like Why Ask (2024)

The best movies like Why Ask (2024) are Lady Windermere's Fan (1925), Hooking Up (2020) and Playing God (2021). If Why Ask hooked you with its comedy and drama, these 30 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. Lady Windermere's Fan (1925)

    A society woman believes her husband is having an affair, a misconception which may have dire personal consequences for all involved.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Popcorn FlickMovies like this
  2. Hooking Up (2020)

    Bailey and Darla embark upon a misguided and mutually deceitful form of therapy, one in which they must drive across the country, re-enacting Darla's colorful history as a sex addict. As their true motivations for the road trip come to light, the unlikely pair force one another to confront their issues, discovering that there might actually be more to love than just sex.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Popcorn FlickMovies like this
  3. Playing God (2021)

    A brother and sister con-artist duo find themselves scamming a grieving billionaire by convincing him they can introduce him to God, face-to-face.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Popcorn FlickMovies like this
  4. My Own Love Song (2010)

    A wheelchair-bound singer and her best friend embark on a roadtrip to Memphis.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Popcorn FlickMovies like this
  5. Almost Friends (2017)

    A man in his mid-20s, still living at home with his mother and stepfather, puts all his eggs in one basket: the girl who works at his local coffee shop. The problem is, she has a serious boyfriend. As they become closer, the line between friendship and intimacy is blurred, and the situation forces both to examine where they are in their lives.

    Why it matches: Recommended by TMDB viewers · both drama & comedy

    Popcorn FlickMovies like this
  6. Landline (2017)

    A teenager living with her sister and parents in Manhattan during the 1990s discovers that her father is having an affair.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Popcorn FlickMovies like this
  7. About Alex (2014)

    When a group of old college friends reunite over a long weekend after one of them attempts suicide, old crushes and resentments shine light on their life decisions, and ultimately push friendships and relationships to the brink.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Popcorn FlickMovies like this
  8. Madea Goes to Jail - The Play (2006)

    Madea returns in another hilarious story in which she gets sent to the big house. But regardless of the circumstances, she gives her trademark advice and wisdom to her friends and family as they learn the importance of letting go, moving on, and forgiveness.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Worth the HypeMovies like this
  9. SubUrbia (1997)

    A group of suburban teenagers try to support each other through the difficult task of becoming adults.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Popcorn FlickMovies like this
  10. CQ (2001)

    A young filmmaker in 1960s Paris juggles directing a cheesy sci-fi debacle, directing his own personal art film, coping with his crumbling relationship with his girlfriend, and a new-found infatuation with the sci-fi film's starlet.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

  11. A Dog Year (2009)

    Jon Katz is close to burnout. He's a writer with writer's block; his wife has left for her sister's because he's emotionally distant; he rarely answers his phone. A kennel sends him a border collie that's undisciplined because of abuse. Despite a series of mishaps, Jon decides to keep trying with the dog, and he rents a dilapidated farm house to give the dog room to run. A local handyman refers Jon to a woman who might be able to help him train the dog. Reluctantly, Jon gives her a try. Is the dog the problem, or the owner?

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Popcorn FlickMovies like this
  12. Somewhere in Queens (2023)

    Leo and Angela Russo live a simple life in Queens, surrounded by their overbearing Italian-American family. When their son finds success on his high school basketball team, Leo tears the family apart trying to make it happen.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Popcorn FlickMovies like this
  13. Standing Up, Falling Down (2020)

    An unlikely friendship kindles between a struggling stand-up comedian from L.A. — forced to move back home to Eastern Long Island with his tail between his legs — and a tragically flawed, but charming and charismatic, alcoholic dermatologist. Discovering to be kindred spirits, each helps the other find healing, in addition to the confidence to face the "failures" in their lives.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Popcorn FlickMovies like this
  14. Six Pack (1982)

    Stopping briefly in a small Texas town, an itinerant race car driver finds that his stock car, on a trailer behind his motor home, has just been quickly and expertly stripped. He chases down the miscreants, who turn out to be six orphan children. He has no recourse to the law, for the corrupt local sheriff takes most of the proceeds of their thievery in exchange for not putting them in an orphanage. They are charming rogues who are in turn charmed by him. Disliking their arrangement with the sheriff, they stow away with him, and he finds himself becoming a reluctant stepfather. Thanks to their enthusiasm and incredible mechanical know-how, he begins to make a name for himself on the racing circuit. But the sheriff doesn't take kindly to losing his extra income...

    Why it matches: Recommended by TMDB viewers · both drama & comedy

    Popcorn FlickMovies like this
  15. Young Adult (2011)

    A divorced writer from the Midwest returns to her hometown to reconnect with an old flame, who's now married with a family.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

  16. It Runs in the Family (2003)

    This is the story of a dysfunctional New York family, and their attempts to reconcile

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Popcorn FlickMovies like this
  17. A Futile and Stupid Gesture (2018)

    In a life full of triumph and failure, "National Lampoon" co-founder Doug Kenney built a comedy empire, molding pop culture in the 1970s.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Popcorn FlickMovies like this
  18. Code 3 (2025)

    A burned-out paramedic tries to survive his last 24 hours on the job while training a new recruit.

    Why it matches: Recommended by TMDB viewers · both comedy & drama

    Worth the HypeMovies like this
  19. Fun with Dick and Jane (1977)

    When an upwardly mobile couple find themselves unemployed and in debt, they turn to armed robbery in desperation.

    Why it matches: Recommended by TMDB viewers · both comedy

    Popcorn FlickMovies like this
  20. John Mulaney: Kid Gorgeous at Radio City (2018)

    John Mulaney relays stories from his childhood and "SNL," eviscerates the value of college and laments getting older in this electric comedy special.

    Why it matches: Recommended by TMDB viewers · both comedy

    Absolute CinemaMovies like this
  21. Chha Maya Chhapakkai (2019)

    The romance between two lovers from opposing political backgrounds whose relationship sparks a massive political revolution and bridges divides within their village.

    Why it matches: Similar story and style · both comedy & drama

  22. Icing on Her Cake (2024)

    A reserved Southeast Asian woman tries to understand the life of her American housemate solely through the groceries of their shared refrigerator and a series of voicemails.

    Why it matches: Similar story and style · both drama & comedy

  23. Load Wedding (2018)

    A guy falls in love but can’t get married before his older sister.

    Why it matches: Similar story and style · both comedy & drama

  24. Relax With Ease (2023)

    A three part meditation.

    Why it matches: Similar story and style · both comedy & drama

  25. Janhit Mein Jaari (2022)

    A small-town girl from MP, Manokamna, gets a decent-paying job. But the work requires her to sell condoms. Will she be able to voice her beliefs while balancing her responsibilities and society?

    Why it matches: Similar story and style · both comedy & drama

  26. What's Up Connection (1990)

    When a Hong Kong teenager from a poor family wins a trip to Japan, he unleashes a chain of events that will soon bring him from his secluded fishing village to Tokyo. On the way, he connects with a barely competent tour guide and a gender-fluid pickpocket. Upon returning home with this merry band of schemers, he and his family of counterfeiters discover that a multinational conglomerate led by a ruthless Japanese developer has found the village, and is determined to raze it to build the new center of world trade.

    Why it matches: Similar story and style · both comedy & drama

  27. Sivaji: The Boss (2007)

    A wealthy engineer arrives in India with the mission of serving the nation and investing in the country's welfare but is met with strong opposition from corrupt officials and politicians. After being faced with insurmountable hardships, he decides to take drastic measures.

    Why it matches: Similar story and style · both drama

    Worth the HypeMovies like this
  28. Divorce Club (2020)

    Ben is devastated when his wife asks for a divorce. While everyone chooses her side, Ben comes across Patrick, an old friend from college, recently divorced. Patrick invites him to crash at his place. The two roommates are soon joined by other divorced, separated and single people looking for a refuge.

    Why it matches: Similar story and style · both comedy

  29. Lost (2024)

    Set in Spanish colonial Philippines. Pedro is tasked to wed a wife whilst his activist friend is considering him to join the revolution. Through a raunchy and campy path of winning the love of his life, Pedro is met with a daunting revelation.

    Why it matches: Similar story and style · both comedy

  30. The Best of Johnny Carson (2010)

    This collection features the most memorable and iconic personality in all of late night television. It includes 21 rare episodes from favorite television classics The Johnny Carson Show, The Johnny Carson Morning Show and Sid Caesar's Hour!

    Why it matches: Similar story and style · both comedy

Like Why Ask and something else?

Blend two favourites and we’ll find the films in between.

Frequently asked questions

What are the best movies like Why Ask?

The closest matches to Why Ask are Lady Windermere's Fan (1925), Hooking Up (2020) and Playing God (2021). Below are 27 more, each with the reason it matches.

What should I watch after Why Ask?

Start with Lady Windermere's Fan (1925), the closest match to Why Ask.

What is the highest-rated movie like Why Ask?

John Mulaney: Kid Gorgeous at Radio City (2018), rated 7.9/10 by 259 TMDB users.

What is the newest movie like Why Ask?

Code 3 (2025) is the most recent release on this list.

How are movies similar to Why Ask chosen?

First come films that Trakt’s viewers watch alongside Why Ask, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.

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