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Movies like Lollipops and Roses (1971)

The best movies like Lollipops and Roses (1971) are Holiday Date (2019), Sailing Into Love (2019) and The Matchmaker's Playbook (2018). If Lollipops and Roses hooked you with its romance, these 20 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. 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
  2. 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
  3. 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
  4. Forever in My Heart (2019)

    Jenna and Charlie found love in Ireland but their dreams drove them apart. Five years later, they reunite and Jenna has to decide where her heart belongs—back home or in the Emerald Isle.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  5. 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
  6. Paris, Wine & Romance (2019)

    Isabella is the ambitious new owner of her family’s Oregon winery whose dream of becoming world-renowned takes a big step forward when she enters a prestigious wine competition in Paris. Upon arrival, Isabella meets her biggest competitor, Jacques, from one of the world’s foremost winemaking families. Impressed by Isabella and her expertise in wine, a budding romance develops between them.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  7. 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
  8. 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
  9. 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
  10. 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
  11. Salsa (1988)

    Fatherless barrio Puerto Rican Rico is a menial car mechanic by day, but lives for the nights, when he dances and dates hot dancing girls, cockily convinced the title of Salsa king in fancy nightclub La Luna's upcoming contest is to be his. He encourages his best friend, courteous gentleman Ken, to date his sister Margarita so he gets a free hand with her flirtatious classmate Lola. The reigning salsa queen Luna's interest in Rico as dance-partner threatens his on-off relationship with Vicki. More jealous trouble follows when Ken and Margarita fall in true love.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this
  12. Taking a Shot at Love (2021)

    Former professional ballet dancer Jenna works with NHL star Ryan Cooper to help him recover from an injury using ballet as therapy, and as they grow close, he helps her mend her injured heart. But when it’s time for Ryan to return to the ice and leave Jenna and her small, Connecticut town, they both must consider the paths they want to take and just maybe, love will find its way.

    Why it matches: Recommended by TMDB viewers · both romance

    Worth the HypeMovies like this
  13. Free Rein: Valentine's Day (2019)

    Love is in the air as Zoe and friends go on a quest to find a fabled Maid's Stone. But when rivalry blinds them to danger, it's Raven to the rescue!

    Why it matches: Recommended by TMDB viewers · both romance

    Worth the HypeMovies like this
  14. It Was Always You (2021)

    Elizabeth's engagement plans are thrown into disarray when her fiancée's free-spirited brother David returns home. David's unexpected influence prompts Elizabeth to question her life decisions.

    Why it matches: Recommended by TMDB viewers · both romance

    Worth the HypeMovies like this
  15. 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
  16. Love and Sunshine (2019)

    Ally Craig has been fostering retired military dog, Sunshine, as she recovers from a broken engagement. But sparks fly again when Sunshine's military partner, Jake Terry, returns to claim the dog.

    Why it matches: Recommended by TMDB viewers · both romance

    Worth the HypeMovies like this
  17. 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
  18. 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
  19. All of My Heart: The Wedding (2018)

    Brian and Jenny are planning their wedding at the Inn where they fell in love. When a distant relative arrives and stakes their claim to the Inn, Brian and Jenny must find a way to save their beloved Inn or risk having to sell.

    Why it matches: Recommended by TMDB viewers · both romance

    Worth the HypeMovies like this
  20. Valentine in the Vineyard (2019)

    As partners in life and professional winemaking, Frankie Baldwin and Nate DeLuca have different personality types and styles. They’ve just gotten engaged when Frankie’s cousin Lexi and Nate’s brother Marco spring the news that they are getting married – and on Valentine’s Day. Agreeing to keep their plans a secret, Frankie and Nate offer to host Lexi and Marco’s big day.

    Why it matches: Recommended by TMDB viewers · both romance

    Popcorn FlickMovies like this

Like Lollipops and Roses and something else?

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

Frequently asked questions

What are the best movies like Lollipops and Roses?

The closest matches to Lollipops and Roses are Holiday Date (2019), Sailing Into Love (2019) and The Matchmaker's Playbook (2018). Below are 17 more, each with the reason it matches.

What should I watch after Lollipops and Roses?

Start with Holiday Date (2019), the closest match to Lollipops and Roses.

What is the newest movie like Lollipops and Roses?

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

How are movies similar to Lollipops and Roses chosen?

First come films that Trakt’s viewers watch alongside Lollipops and Roses, 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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