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Movies like Transgendered Bosses (2019)

The best movies like Transgendered Bosses (2019) are The Matchmaker's Playbook (2018), Gabriel's Rapture: Part I (2021) and Gabriel's Rapture: Part II (2022). If Transgendered Bosses 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. 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
  3. Gabriel's Rapture: Part II (2022)

    In the fifth installment of the Gabriel's Inferno series, Gabriel and Julia’s happiness is threatened by a conspiring student and academic politics. When Gabriel is confronted by the university administration, will he succumb to Dante's fate? Or will he fight to keep Julia, his Beatrice, forever?

    Why it matches: Recommended by TMDB viewers · both romance

    Absolute CinemaMovies like this
  4. 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
  5. Gabriel's Rapture: Part III (2022)

    In the sixth installment of the Gabriel's Inferno series, Julia deals with the aftermath of Gabriel's departure, while Gabriel goes on a journey of self-discovery. Will they reunite and be able to repair what is broken?

    Why it matches: Recommended by TMDB viewers · both romance

    Absolute CinemaMovies like this
  6. 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
  7. Frequencies (2013)

    The story of the forbidden relationship between a 'low born' boy and a 'high born' girl in an alternate reality where every person's relationships and life worth are determined by their innate 'frequencies'.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  8. 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
  9. 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
  10. Chateau Christmas (2020)

    Margot, a world-renowned pianist, returns to Chateau Newhaus to spend the holidays with her family and is reunited with an ex who helps her rediscover her passion for music.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  11. Last Chance for Christmas (2015)

    When Prancer injures his hoof Santa’s stable hand, John, must find a fill in to ensure Christmas deliveries go off without a hitch. His mission gets complicated when he discovers that Frankie, the perfect substitute reindeer, belongs to a precocious 8-year-old girl and her mother Annie. As he races to get Frankie up to the North Pole, he realizes that he’s actually falling in love with Annie and has to find a way to win her over and save Christmas at the same time.

    Why it matches: Recommended by TMDB viewers · both romance

  12. Sense, Sensibility & Snowmen (2019)

    Christmas enthusiast party planners Ella and her sister, Marianne, clash with their client, Edward, who is a not-so-jolly toy company CEO.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  13. Scaramouche (1952)

    In 18th-century France, a young man masquerades as an actor to avenge his friend's murder.

    Why it matches: Recommended by TMDB viewers · both romance

    Worth the HypeMovies like this
  14. 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
  15. Double Holiday (2019)

    Rebecca must throw the company holiday party with office rival, Chris. It coincides with Hanukkah, so she must juggle her work, family traditions, and nemesis to make the party a success.

    Why it matches: Recommended by TMDB viewers · both romance

    Worth the HypeMovies like this
  16. The Baker's Son (2021)

    Matt’s passion transforms his bread from bland to brilliant. But when his bread loses its magic, the island locals panic and turn to Annie - Matt’s childhood friend and true love - for help.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  17. 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
  18. The World in His Arms (1952)

    A boisterous sea captain in the Pacific Coast, circa 1850, has a plan to buy Alaska from the Russians… if they don’t kill him first.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  19. 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
  20. All of My Heart: Inn Love (2017)

    Brian and Jenny are preparing for the grand opening of their bed and breakfast, Emily's Country Inn, when a big storm hits Buck County. Brian agrees to go back to Wall Street to boost their funds, while Jenny scrambles to keep the opening on track.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this

Like Transgendered Bosses and something else?

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

Frequently asked questions

What are the best movies like Transgendered Bosses?

The closest matches to Transgendered Bosses are The Matchmaker's Playbook (2018), Gabriel's Rapture: Part I (2021) and Gabriel's Rapture: Part II (2022). Below are 17 more, each with the reason it matches.

What should I watch after Transgendered Bosses?

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

What is the highest-rated movie like Transgendered Bosses?

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

What is the newest movie like Transgendered Bosses?

Gabriel's Rapture: Part III (2022) is the most recent release on this list.

Are there English movies like Transgendered Bosses?

Yes: The Matchmaker's Playbook (2018), Gabriel's Rapture: Part I (2021) and Gabriel's Rapture: Part II (2022).

How are movies similar to Transgendered Bosses chosen?

First come films that Trakt’s viewers watch alongside Transgendered Bosses, 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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