Movies like The Sleepless (2020)
The best movies like The Sleepless (2020) are The Matchmaker's Playbook (2018), Holiday Date (2019) and Sailing Into Love (2019). If The Sleepless hooked you with its romance, these 20 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedEvery Day (2018)7.2/10 from 2,334 votes
- NewestJune and John (2025)Released 2025
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 thisHoliday 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 thisSailing 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 thisParis, 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 thisSisters 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 thisLove in Winterland (2020)
Ally, a final contestant on a dating show, must face her high school sweetheart when she is chosen for the Hometown Date.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisIt 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 thisMatching 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 thisAttraction (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 thisA 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 thisValentine 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 thisRome in Love (2019)
An unknown actress lands the role of a lifetime in Rome. Paired with an American journalist writing a profile, she will discover surprises about love and life in the eternal city.
Why it matches: Recommended by TMDB viewers · both romance
Popcorn FlickMovies like thisForever 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 thisTaking 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 thisSecret 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 thisEvery 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 thisAll 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 thisA Godwink Christmas: Meant For Love (2019)
Multiple coincidences and a chance meeting bring together Alice and Jack, two strangers from very different family backgrounds, for an unexpected Christmastime courtship filled with personal revelations, misread signals, and a very real health scare that will either destroy or strengthen the budding romance.
Why it matches: Recommended by TMDB viewers · both romance
Worth the HypeMovies like thisSafe Haven (2013)
A young woman with a mysterious past lands in Southport, North Carolina where her bond with a widower forces her to confront the dark secret that haunts her.
Why it matches: Recommended by TMDB viewers · both romance
Worth the HypeMovies like thisJune and John (2025)
John leads an ordinary life with a monotonous routine. One day John runs into a woman on the subway who is as beautiful as she is mysterious named June. His encounter with her finally leads him to have a goal in his bumptious life.
Why it matches: Recommended by TMDB viewers · both romance
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Frequently asked questions
What are the best movies like The Sleepless?
The closest matches to The Sleepless are The Matchmaker's Playbook (2018), Holiday Date (2019) and Sailing Into Love (2019). Below are 17 more, each with the reason it matches.
What should I watch after The Sleepless?
Start with The Matchmaker's Playbook (2018), the closest match to The Sleepless.
What is the highest-rated movie like The Sleepless?
Every Day (2018), rated 7.2/10 by 2,334 TMDB users.
What is the newest movie like The Sleepless?
June and John (2025) is the most recent release on this list.
Are there English movies like The Sleepless?
Yes: The Matchmaker's Playbook (2018), Holiday Date (2019) and Sailing Into Love (2019).
How are movies similar to The Sleepless chosen?
First come films that Trakt’s viewers watch alongside The Sleepless, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.