Movies like Cherry Boy
The best movies like Cherry Boy are Which Brings Me to You (2023), The Best You Can (2025) and The Half of It (2020). If Cherry Boy hooked you with its romance and comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Cherry Boy
Quick picks
- Highest ratedThe Lady Eve (1941)7.3/10 from 422 votes
- NewestRelationship Goals (2026)Released 2026
- In KoreanYou Are the Apple of My Eye (2025)Also in Korean
Which Brings Me to You (2023)
Two romantic burnouts, Jane and Will, are immediately drawn to each other at a mutual friend’s wedding. After a disastrous hookup in the coatroom, the two spend the next 24 hours together, trading candid confessions of messy histories and heartbreak, on the off chance that this fling might be the real thing.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Best You Can (2025)
Cynthia Rand is a buttoned-up New Yorker married to a brilliant professor 25 years her senior. She begins feeling the effects of her husband’s advancing age on their relationship, just as her world is turned upside down by the arrival of sharp but chronically underachieving security guard Stan Olszewski in this smart rom-com that reunites Bacon and Sedgwick on screen for the first time in 20 years.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisThe Half of It (2020)
Shy, straight-A student Ellie is hired by sweet but inarticulate jock Paul, who needs help wooing the most popular girl in school. But their new and unlikely friendship gets tricky when Ellie discovers she has feelings for the same girl.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisA California Christmas (2020)
With his carefree lifestyle on the line, a wealthy charmer poses as a ranch hand to get a hardworking farmer to sell her family’s land before Christmas.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisYou Are the Apple of My Eye (2025)
A group of close friends who attend a private school all have a debilitating crush on the sunny star pupil, Sun-ah. The only member of the group who claims not to is Jin-woo, but he ends up loving her as well.
Why it matches: Recommended by TMDB viewers · both romance & drama
Absolute CinemaMovies like thisRosaline (2022)
Left heartbroken after Romeo begins to pursue her cousin Juliet, Rosaline schemes to foil the famous romance and win back her guy in this comedic twist of Shakespeare's Romeo and Juliet.
Why it matches: Recommended by TMDB viewers · both romance & drama
Worth the HypeMovies like thisSidewalks of New York (2001)
The film follows the marital and dating lives of three men and three women who unknowingly form a tangled web of relationships. Interspersing "man on the street" interviews with scenes from the six characters' lives, the film weaves a humorous and biting commentary on the game of love -- easy to start, hard to finish.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisL.A. Without a Map (1999)
An aspiring Hollywood actress, on a visit to a charming North England town, has a brief fling with the town undertaker, who also writes obituaries for the local paper. Returning home, where she works as a waitress at a Japanese restaurant, she tells everyone about the handsome "writer" she met on her trip. Unfortunately, he decides to follow her back to Hollywood, setting up the expected light romantic comedy with asides as the newcomer gains experience about the goings on in Hollywood.
Why it matches: Recommended by TMDB viewers · both drama & comedy
SnoozefestMovies like thisTall Girl (2019)
Jodi, the tallest girl in her high school, has always felt uncomfortable in her own skin. But after years of slouching, being made fun of, and avoiding attention at all costs, Jodi finally decides to find the confidence to stand tall.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisLove Lesson (2013)
Korea's most popular song writer Hee-soo runs into a nineteen-year-old boy in the elevator. Hee-soo is inspired by a new song watching him shake at her figure. She starts to tell him about women under the excuse that she's teaching him music. They fall for each other but things get complicated when her life teacher, Joon-ho who taught her about life and music comes back.
Why it matches: Recommended by TMDB viewers · both romance & drama
Popcorn FlickMovies like thisXX/XY (2002)
Three friends begin a dangerous three-way relationship that spirals out of control, leading to dire consequences that haunt them ten years later.
Why it matches: Recommended by TMDB viewers · both drama & comedy
Popcorn FlickMovies like thisThe Other Sister (1999)
A mentally challenged girl proves herself to be every bit as capable as her "perfect" sister when she moves into an apartment and begins going to college.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Popcorn FlickMovies like thisDrive Me Crazy (1999)
Nicole and Chase live next door to each other but are worlds apart. However, they plot a scheme to date each other in order to attract the interest and jealousy of their respective romantic prey. But in the mist of planning a gala centennial celebration, Nicole and Chase find that the one they always wanted was closer than they ever thought.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisMadame (2017)
Anne and Bob, a well-to-do American couple, have just moved to a beautiful manor house in romantic Paris. To impress their sophisticated friends, they decide to host a lavish dinner party, but must disguise their maid as a noblewoman to even out the number of guests. When the maid runs off with a wealthy guest, Anne must chase her around Paris to thwart the joyous and unexpected love affair.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisRelationship Goals (2026)
When TV producer Leah Caldwell aims to become the first woman running New York's top morning show, her ex competes for the same role. Leah stays focused on her career, until chemistry with her ex challenges her priorities.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisDean (2016)
A comedy about loss, grief, and the redemptive power of love. Dean is a NY illustrator who falls hard for an LA woman while trying to prevent his father from selling the family home in the wake of his mother's death.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisWhat's Love Got to Do with It? (2023)
Two childhood friends now in their thirties must decide whether to follow their heads or their hearts once the man decides to follow his parents' advice and enter into an arranged marriage in Pakistan.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like this10 Years (2012)
A group of friends reunite ten years after their high-school graduation.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisI Love You Again (1940)
Boring businessman Larry Wilson recovers from amnesia and discovers he's really a con man...and loves his soon-to-be-ex wife.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisLove Is in the Air (2023)
A fiercely independent pilot fighting to keep her family business afloat starts to fall for the man sent by corporate to ground her operation forever.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisThe Private Lives of Pippa Lee (2009)
After her much older husband forces a move to a suburban retirement community, Pippa Lee engages in a period of reflection and finds herself heading toward a quiet nervous breakdown.
Why it matches: Similar story and style · both comedy & drama
SnoozefestMovies like thisSex and the City (2008)
When Carrie's big step forward in her relationship goes awry, best friends Charlotte, Miranda and Samantha are there to help her pick up the pieces.
Why it matches: Similar story and style · both comedy & drama
Popcorn FlickMovies like thisA Lot Like Love (2005)
On a flight from Los Angeles to New York, Oliver and Emily make a connection, only to decide that they are poorly suited to be together. Over the next seven years, however, they are reunited time and time again, they go from being acquaintances to close friends to... lovers?
Why it matches: Similar story and style · both comedy & drama
Popcorn FlickMovies like thisLivin' with the Devil (2025)
After a recent breakup, a couple finds themselves financially trapped under the same roof, navigating the complexities of living together while separated.
Why it matches: Similar story and style · both comedy & drama
The Lady Eve (1941)
It's no accident when wealthy Charles falls for Jean. Jean is a con artist with her sights set on Charles' fortune. Matters complicate when Jean starts falling for her mark. When Charles suspects Jean is a gold digger, he dumps her. Jean, fixated on revenge and still pining for the millionaire, devises a plan to get back in Charles' life. With love and payback on her mind, she re-introduces herself to Charles, this time as an aristocrat named Lady Eve Sidwich.
Why it matches: Similar story and style · both comedy & romance
Worth the HypeMovies like thisGrease 2 (1982)
It's 1961, two years after the original Grease gang graduated, and there's a new crop of seniors and new members of the coolest cliques on campus, the Pink Ladies and T-Birds. Michael Carrington is the new kid in school - but he's been branded a brainiac. Can he fix up an old motorcycle, don a leather jacket, avoid a rumble with the leader of the T-Birds, and win the heart of Pink Lady Stephanie?
Why it matches: Similar story and style · both comedy & romance
SnoozefestMovies like thisThe Thing About Harry (2020)
Two high school enemies, uber-jock Harry and out-and-proud Sam, are forced to share a car ride to their Missouri hometown for a friend's engagement party on Valentine's Day. Things take a turn when Sam learns Harry has come out.
Why it matches: Similar story and style · both romance & comedy
Popcorn FlickMovies like thisJust Like Heaven (2005)
Shortly after David Abbott moves into his new San Francisco digs, he has an unwelcome visitor on his hands: winsome Elizabeth Masterson, who asserts that the apartment is hers -- and promptly vanishes. When she starts appearing and disappearing at will, David thinks she's a ghost, while Elizabeth is convinced she's alive.
Why it matches: Similar story and style · both comedy & romance
Worth the HypeMovies like thisWhat Happens in Vegas (2008)
During a wild vacation in Las Vegas, career woman Joy McNally and playboy Jack Fuller come to the sober realization that they have married each other after a night of drunken abandon. They are then compelled, for legal reasons, to live life as a couple for a limited period of time. At stake is a large amount of money.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisBoating in Tehran (2026)
It's about a man who returns to iran after many years and the feeling of old love awakens in his heart in the beautiful atmosphere of Tehran.
Why it matches: Similar story and style · both romance & comedy
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Frequently asked questions
What are the best movies like Cherry Boy?
The closest matches to Cherry Boy are Which Brings Me to You (2023), The Best You Can (2025) and The Half of It (2020). Below are 27 more, each with the reason it matches.
What should I watch after Cherry Boy?
Start with Which Brings Me to You (2023), the closest match to Cherry Boy.
What is the highest-rated movie like Cherry Boy?
The Lady Eve (1941), rated 7.3/10 by 422 TMDB users.
What is the newest movie like Cherry Boy?
Relationship Goals (2026) is the most recent release on this list.
Are there Korean movies like Cherry Boy?
Yes: You Are the Apple of My Eye (2025) and Love Lesson (2013).
How are movies similar to Cherry Boy chosen?
First come films that Trakt’s viewers watch alongside Cherry Boy, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.