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Movies like Stupid Questions (2011)

The best movies like Stupid Questions (2011) are The Matchmaker's Playbook (2018), Secret Millionaire (2018) and Holiday Date (2019). If Stupid Questions hooked you with its romance, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. The Matchmaker's Playbook (2018)

    After a career-ending accident, former NFL recruit Ian Hunter is back on campus, and he's putting his extensive skills with women to work as one of the masterminds behind a successful and secretive dating service. But when Blake Olson requests the services of Wingmen, Inc., Ian may have landed his most hopeless client yet. As Blake begins the transformation from hot mess to smokin' hot, Ian realizes he's in danger of breaking his cardinal rule....

    Why it matches: Recommended by TMDB viewers · both romance

    Worth the HypeMovies like this
  2. Secret Millionaire (2018)

    When a bored millionaire (Steve Lund) is mistaken for a parking attendant by a beautiful girl (Siobhan Williams) who is protesting against his family’s intention of closing a local park, he uses the misunderstanding to get to know her better.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  3. Holiday Date (2019)

    When Brooke’s boyfriend, Ethan, breaks up with her just before the holidays, she agrees to go home with Joel, an actor who will pose as her boyfriend.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  4. Attraction (2001)

    A writer/radio advice show host fails to heed his own advice as he stalks his ex-girlfriend and then becomes involved with an actress friend of hers.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  5. Turkey Drop (2019)

    Lucy Jacobs, a freshman university student, returns home to her small town for Thanksgiving break and suspects she's about to get turkey dropped— aka dumped by her high school sweetheart. To avoid a Turkey Day travesty, Lucy gets out of her comfort zone, proving she's not the same play-it-safe girl she once was.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  6. Sisters of the Groom (2017)

    When Sarah needs to impress a corporate bigwig in order to help her sister's catering business, she finds herself agreeing to be his son’s pretend date to a family wedding

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  7. Project Christmas Wish (2020)

    For years Lucy has played Santa to her small town’s community by making their holiday wishes come true. But when Lucy grants a little girl’s wish for a Christmas like she used to have with her mom, she unexpectedly finds her own wishes coming true in life and love.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  8. Valentine Ever After (2016)

    Big city girls Julia and her best friend Sydney take a trip to a dude ranch in Wyoming for a fun weekend getaway, but after a brawl at the local bar, the girls are sentenced to stay in town and perform community service. Along the way, Julia finds love and her true calling in life.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  9. Every Day (2018)

    16-year old Rhiannon falls in love with a mysterious spirit named “A” that inhabits a different body every day. Feeling an unmatched connection, Rhiannon and “A” work each day to find each other, not knowing what the next day will bring.

    Why it matches: Recommended by TMDB viewers · both romance

    Worth the HypeMovies like this
  10. Gabriel's Rapture: Part I (2021)

    In the fourth instalment of the Gabriel's Inferno series, Professor Gabriel Emerson has embarked on a passionate, yet clandestine affair with his former student Julia Mitchell, but when they return from their romantic holiday in Italy, their happiness is threatened. Will Gabriel succumb to Dante's fate?

    Why it matches: Recommended by TMDB viewers · both romance

    Worth the HypeMovies like this
  11. Sailing Into Love (2019)

    A biology teacher’s crusade to save a nearby island from development leads to unexpected romance with the handsome and mysterious young sea captain who is new to the seaside town of Willow Bay.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  12. Matching Hearts (2020)

    As Valentine's Day nears, a matchmaker is tasked by her mentor to find a match for an entrepreneur who believes staying single is the key to success.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  13. A Gift to Remember (2017)

    After colliding with a pedestrian on her bicycle who loses his memory following the accident, Darcy Archer becomes determined to help the handsome guy figure out who he is. In the process, she finds out a lot more about who she is, what she wants from life, and how this too-good-to-be-true guy might just be the man she’s been waiting to bump into all her life.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  14. The Tourist (2010)

    American tourist Frank meets mysterious British woman Elise on the train to Venice. Romance seems to bud, but there's more to her than meets the eye.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  15. X (2011)

    A veteran call girl and a runaway prostitute witness a murder which sends them on an out-of-control roller coaster ride through the twilight zone of sex-for-sale.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  16. Brigadoon (1954)

    Americans Jeff and Tommy, hunting in Scotland, stumble upon a village - Brigadoon. They soon learn that the town appears once every 100 years in order to preserve its peace and special beauty. The citizens go to bed at night and when they wake up, it's 100 years later. Tommy falls in love with a beautiful young woman, Fiona, and is torn between staying or going back to his hectic life in New York.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  17. Marry Me at Christmas (2017)

    Organizing a Christmas wedding is a true treat for bridal boutique owner Madeline Krug. She loves the challenge of finding the perfect dress for the bride and orchestrating an exquisite event. What Madeline didn’t expect was to be swept off her feet by the bride’s gorgeous brother, movie star, Jonny Blaze. Jonny came to the quirky town of Fool’s Gold to support his sister -- not to fall in love. Yet Madeline is the most extraordinary woman he’s ever met, and she finds the real Jonny even more captivating than her celebrity crush. Will the action star be brave enough to take on the role of a lifetime?

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  18. A Country Wedding (2015)

    A famous country singer set to marry a glamorous Hollywood actress returns to his small town roots. When he crosses paths with his childhood sweetheart and finally feels inspired to write songs again he reevaluates his life, his values and his opinion of true love. As his wedding day approaches, he must decide if he has chosen the right woman to be his wife.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  19. A Little Christmas Charm (2020)

    Holly, a jewelry designer finds a lost charm bracelet and teams up with investigative reporter Greg in hopes of finding the owner and returning it by Christmas Eve.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  20. Love at First Bark (2017)

    Portland interior designer Julia Galvins (Jana Kramer) adopts a dog and seeks the help of expert and handsome dog trainer Owen Michaels (Kevin McGarry). When she is hired to design a nursery and a “puppery,” as well as plan a puppy shower fund-raiser for a pregnant client and her pregnant dog, Julia asks Owen’s advice, and their friendship just might turn into something more.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this

Like Stupid Questions and something else?

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

Frequently asked questions

What are the best movies like Stupid Questions?

The closest matches to Stupid Questions are The Matchmaker's Playbook (2018), Secret Millionaire (2018) and Holiday Date (2019). Below are 17 more, each with the reason it matches.

What should I watch after Stupid Questions?

Start with The Matchmaker's Playbook (2018), the closest match to Stupid Questions.

What is the highest-rated movie like Stupid Questions?

Gabriel's Rapture: Part I (2021), rated 7.8/10 by 200 TMDB users.

What is the newest movie like Stupid Questions?

Gabriel's Rapture: Part I (2021) is the most recent release on this list.

Are there English movies like Stupid Questions?

Yes: The Matchmaker's Playbook (2018), Secret Millionaire (2018) and Holiday Date (2019).

How are movies similar to Stupid Questions chosen?

First come films that Trakt’s viewers watch alongside Stupid Questions, 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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