Movies like You're a Big Boy Now (1966)
The best movies like You're a Big Boy Now (1966) are A Nice Girl Like You (2020), My Sassy Girl (2008) and Little Italy (2018). If You're a Big Boy Now hooked you with its comedy and romance, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest rated¿Quieres ser mi hijo? (2023)8.4/10 from 378 votes
- NewestYoh! Bestie (2026)Released 2026
A Nice Girl Like You (2020)
Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her on a whirlwind and surprising journey of self-discovery, friendship, and new love.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisMy Sassy Girl (2008)
A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisLittle Italy (2018)
Former childhood pals Leo and Nikki are attracted to each other as adults—but will their feuding parents' rival pizzerias put a chill on their sizzling romance?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe Incredible Jessica James (2017)
Burned by a bad breakup, a struggling New York City playwright makes an unlikely connection with a divorced app designer she meets on a blind date.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisSex Appeal (2022)
Avery, a teenager with a tendency towards perfectionism, enlists her friend Larson to help her prepare for her first time with her long-distance boyfriend.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisHow to Be Single (2016)
New York City is full of lonely hearts seeking the right match, and what Alice, Robin, Lucy, Meg, Tom and David all have in common is the need to learn how to be single in a world filled with ever-evolving definitions of love.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisSomeone Great (2019)
An aspiring music journalist lands her dream job and is about to move to San Francisco when her boyfriend of nine years decides to call it quits. To nurse her broken heart, she and her two best friends spend one outrageous last adventure in New York City.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like this¿Quieres ser mi hijo? (2023)
Lu, a conformist woman in her forties, learns that her 15-year partner has been having extramarital affairs. Starting from scratch, she gets involved in an unexpected relationship with a young womanizer.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Absolute CinemaMovies like thisSilk Stockings (1957)
After three bumbling Soviet agents fail in their mission to retrieve a straying Soviet composer from Paris, the beautiful, ultra-serious Ninotchka is sent to complete their mission and to retrieve them. She starts out condemning the decadent West, but gradually falls under its spell—with the help of an American movie producer. A remake of Ninotchka (1939).
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisChristmas with You (2022)
Feeling career burnout, pop star Angelina escapes to grant a young fan's wish in small-town New York, where she not only finds the inspiration to revitalize her career but also a shot at true love.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisPuppy Love (2023)
After a disastrous first date, wild-child Nicole and socially-anxious Max vow to lose each other’s numbers until they learn that their dogs found a love match, and now puppies are on the way! The hilariously mismatched Nicole and Max are forced to become responsible co-parents, but may end up finding love themselves.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisSplendor (1999)
Veronica is a white-bread beauty searching for a good man in Los Angeles. While slam dancing at a Halloween rave, she meets Abel, a sensitive poet. Then she meets Zed, a supersexy tattooed drummer with incredible biceps. Who will she choose? Does she go for true love or cheap sex? She can't decide so she chooses both. But after managing to nurture a picture-perfect threesome, along comes Ernest, a rich movie director with deep baby blues that sweep Veronica off her feet. What's a girl to do now?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisCrossing Delancey (1988)
Thirty-something Isabelle spends her time going from her tiny, solitary West Side apartment to that of her grandmother on the Lower East Side. While her grandmother plots to find her a romantic match, Isabelle is courted by a married, worldly author, Anton, yet can't seem to shake the down-to-earth appeal of Sam, a pickle vendor.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisDesperados (2020)
A panicked young woman and her two best friends fly to Mexico to delete a ranting email she sent to her new boyfriend. On arrival, they run into her former beau, who soon gets caught up in their frantic scheme.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisLong Weekend (2021)
Bart's chance encounter with the enigmatic Vienna leads to a whirlwind weekend together. The two fall fast and hard, but both carry secrets that could be their undoing or the chance for a fresh start.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisLet's Make Love (1960)
When billionaire Jean-Marc Clement learns that he is to be satirized in an off-Broadway revue, he passes himself off as an actor playing him in order to get closer to the beautiful star of the show, Amanda Dell.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisEasy Virtue (2008)
A young Englishman marries a glamorous American. When he brings her home to meet the parents, she arrives like a blast from the future - blowing their entrenched British stuffiness out the window.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisPlayers (2024)
New York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it takes to go from simply scoring to playing for keeps.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisYoh! Bestie (2026)
Thando is perpetually unlucky in love, but when her bestie returns from his travels with a fiancée in tow, she's forced to face a new emotion — jealousy.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisLove, Weddings & Other Disasters (2020)
A fussy celebrity caterer, a blind woman, a tour-bus guide and an inexperienced wedding planner search for love.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisBreakfast at Tiffany's (1961)
Holly Golightly is an eccentric New York City playgirl determined to marry a Brazilian millionaire. But when young writer Paul Varjak moves into her apartment building, her past threatens to get in their way.
Why it matches: Similar story and style · both comedy & romance
Worth the HypeMovies like thisThe Apartment (1960)
Bud Baxter is a minor clerk in a huge New York insurance company, until he discovers a quick way to climb the corporate ladder. He lends out his apartment to the executives as a place to take their mistresses. Although he often has to deal with the aftermath of their visits, one night he's left with a major problem to solve.
Why it matches: Similar story and style · both comedy & romance
Absolute CinemaMovies like thisManhattan (1979)
Manhattan explores how the life of a middle-aged television writer dating a teenage girl is further complicated when he falls in love with his best friend's mistress.
Why it matches: Similar story and style · both comedy & romance
Worth the HypeMovies like thisWhen Harry Met Sally... (1989)
Sex always gets in the way of friendships between men and women. At least, that's what Harry Burns believes. So when Harry meets Sally Albright and a deep friendship blossoms between them, Harry's determined not to let his attraction to Sally destroy it. But when a night of weakness ends in a morning of panic, can the pair avoid succumbing to Harry's fears by remaining friends and admitting they just might be the perfect match for each other?
Why it matches: Similar story and style · both comedy & romance
Worth the HypeMovies like thisAnnie Hall (1977)
New York comedian Alvy Singer falls in love with the ditsy Annie Hall.
Why it matches: Similar story and style · both comedy & romance
Worth the HypeMovies like thisPocketful of Miracles (1961)
A New York gangster and his girlfriend attempt to turn street beggar Apple Annie into a society lady when the peddler learns her daughter is marrying royalty.
Why it matches: Similar story and style · both comedy
Worth the HypeMovies like thisEternal Sunshine of the Spotless Mind (2004)
Joel Barish, heartbroken that his girlfriend underwent a procedure to erase him from her memory, decides to do the same. However, as he watches his memories of her fade away, he realises that he still loves her, and may be too late to correct his mistake.
Why it matches: Similar story and style · both romance
Absolute CinemaMovies like thisWings of Desire (1987)
Two angels, Damiel and Cassiel, glide through the streets of Berlin, observing the bustling population, providing invisible rays of hope to the distressed but never interacting with them. When Damiel falls in love with lonely trapeze artist Marion, the angel longs to experience life in the physical world, and finds — with some words of wisdom from actor Peter Falk — that it might be possible for him to take human form.
Why it matches: Similar story and style · both romance
Worth the HypeMovies like thisPeacock Alley (1930)
Show dancer Claire finds herself in the New York hotel-suite with Stoddard Clayton, saying goodbye to him before her impending marriage the following day. When she returns to the hotel with her husband the following night, the house detective accuses her of prostitution and throws them out. Now Claire must explain everything to her unsympathetic husband.
Why it matches: Similar story and style · both romance
Too Much Harmony (1933)
A singer is involved with two women in his life, one a "good" girl and one a "bad" one."
Why it matches: Similar story and style · both comedy
Like You're a Big Boy Now and something else?
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Frequently asked questions
What are the best movies like You're a Big Boy Now?
The closest matches to You're a Big Boy Now are A Nice Girl Like You (2020), My Sassy Girl (2008) and Little Italy (2018). Below are 27 more, each with the reason it matches.
What should I watch after You're a Big Boy Now?
Start with A Nice Girl Like You (2020), the closest match to You're a Big Boy Now.
What is the highest-rated movie like You're a Big Boy Now?
¿Quieres ser mi hijo? (2023), rated 8.4/10 by 378 TMDB users.
What is the newest movie like You're a Big Boy Now?
Yoh! Bestie (2026) is the most recent release on this list.
Are there English movies like You're a Big Boy Now?
Yes: A Nice Girl Like You (2020), My Sassy Girl (2008) and Little Italy (2018).
How are movies similar to You're a Big Boy Now chosen?
First come films that Trakt’s viewers watch alongside You're a Big Boy Now, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.