Movies like Crossing Hennessy (2010)
The best movies like Crossing Hennessy (2010) are Chasing Papi (2003), The Prince & Me 4: The Elephant Adventure (2010) and Crossing Delancey (1988). If Crossing Hennessy 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 ratedThe Wrong Paris (2025)6.7/10 from 359 votes
- NewestYoh! Bestie (2026)Released 2026
Chasing Papi (2003)
Playboy Thomas Fuentes has so far been able to skate by in life on good looks and charm alone. But when his duplicitous relationships with three women -- impassioned waitress Cici, meticulous lawyer Lorena and bored socialite Patricia -- spiral out of control, he suffers a mental breakdown. His doctor recommends that he choose just one girlfriend -- but can he choose in time before they discover his deception?
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe Prince & Me 4: The Elephant Adventure (2010)
One year after their royal wedding, King Edvard and Queen Paige of Denmark receive an invitation to attend the wedding of Princess Myra of Sangyoon. Upon their arrival, Paige finds Myra is unhappy with her arranged marriage to the brooding and sinister Kah and is secretly in love with a young elephant handler named Alu.
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 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 thisWedding Season (2022)
Pressured by their immigrant parents to find spouses, two Indian-Americans pretend to date in order to survive a summer of weddings – but find themselves falling for each other as they struggle to balance who they are with who their parents want them to be.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies 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 thisYou Cast A Spell On Me (2015)
Despite agreeing to an arranged marriage to a childhood friend, a successful businessman tries to track down a beautiful woman that he met at a Halloween party.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies 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 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 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 thisLove in the Buff (2012)
When old flames reunite, will it be second time's the charm or a case of once bitten twice shy? Jimmy and Cherie, two ex-lovers from Hong Kong, cross paths in Beijing and can't seem to forget each other, despite being involved with someone else. Torn between fidelity towards their new partners or following their hearts, they explore the struggles, doubts and fears that exist among modern young couples.
Why it matches: Recommended by TMDB viewers · both comedy & romance
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 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 thisThe Wrong Paris (2025)
Dawn thinks she's joining a dating show in Paris, France, only to land in Paris, Texas. She has an exit plan — until sparks fly with the cowboy bachelor.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisStarting Over (1979)
After divorcing his ambitious singer wife, a middle-aged man begins a new relationship with a teacher.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisBye Bye Love (1995)
With varying degrees of success, recently divorced friends Dave, Vic and Donny are trying to move on with their lives. Vic feels vilified by his ex-wife's parents, while Donny has a shaky bond with his teen daughter, Emma. Dave, meanwhile, has an enviable problem -- he has more dates than he can handle. As they confront their post-marital challenges, the men take solace in one another's plights.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisA 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 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 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 thisReturn to Me (2000)
It took a lot of persuading to get Bob, a recently widowed architect, to go on a blind date at a quirky Irish-Italian eatery. Once there, he’s instantly smitten, not with his date, but with the sharp-witted waitress. Everything seems to be going great until an unbelievable truth is revealed, one that could easily break both of their hearts for good.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisButch Jamie (2008)
The film follows the story of Jamie, a struggling butch lesbian actress who gets cast as a man in a film. The main plot is a romantic comedy between Jamie's male alter-ego, "Male Jamie," and Jill, a heterosexual woman on set. The film's subplots include Jamie's bisexual roommate Lola and her cat actor Howard, Lola's abrasive butch German girlfriend Andi, and Jamie's gay Asian friend David.
Why it matches: Similar story and style · both comedy & romance
Cinderella (1947)
In the fairy kingdom live stepmother, her evil daughters — Anna and Maryana, a limp husband-forester and his daughter from his first marriage — Cinderella. The stepmother exploits the poor girl as a housekeeper. With the help of her godmother-fairy, Cinderella gets to the royal ball, where a beautiful and very kind prince falls in love with her. At midnight, the magic ends, and poor Cinderella has to return to her former life. But on the crystal shoe that Cinderella lost while fleeing the palace to the battle of the palace chimes, the prince searches for the bride.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisMILF (2018)
Three childhood friends - Elise, Sonia and Cecile - leave for a summer in the South of France to help clear Cecile’s holiday house before it is put up for sale. There, they soon become the prime targets of three horny young men, for whom these single forty-year-old women are much more attractive than girls their age.
Why it matches: Similar story and style · both comedy & romance
SnoozefestMovies like this12 Men of Christmas (2009)
A high-powered New York publicist finds herself in Montana promoting a charity calendar after being betrayed by her boss and fiancé. Unfortunately, matters of the heart are just as complicated in the wilds as they are in the big city.
Why it matches: Similar story and style · both comedy & romance
SnoozefestMovies like thisDrop Dead Roses (2002)
Everyguy Shawn and his buddy Jason have tapped into a unique market and figured out how to turn it into a successful business: They get revenge on your ex by delivering dead roses or mistreated chocolates, accompanied by a nasty message. But things get complicated when Shawn must make a delivery to Kayla -- a woman he's been infatuated with.
Why it matches: Similar story and style · both comedy & romance
Christopher Walken's Coffee Shop (2016)
Christopher Walken has branched out from his very successful acting career to pursue his true passion, creating artisanal coffee beverages and pastries, but be warned his concoctions have more than just meets the eye.
Why it matches: Similar story and style · both comedy
Der Duft von Holunder (2011)
Once Sofie Möller left her idyllic hometown with the aim of making a career in the big city. Now she returns with her mother Agnes to attend the funeral of her grandmother and to revamp her empty house for sale. It does not take long for Sofie to be confronted with her past, which apart from the grandmotherly love consisted of many personal injuries. When she meets her former boyhood friend Tom Sommer again, Sofie has come to the time to rethink her own emotional life.
Why it matches: Similar story and style · both romance
The Christmas Secret (2014)
While her life is falling apart, single mother Christine finds a magical family heirloom that leads to love and good fortune during Christmas.
Why it matches: Similar story and style · both romance
Popcorn FlickMovies like thisBut Muzeyyen That's the Deepest Desire (2014)
Arif, who is trying to write his first book, believes that life contains many unanswerable questions, especially about women and relationships. But when Müzeyyen appears unexpectedly, everything he has ever known or tried to learn is suddenly turned upside down.
Why it matches: Similar story and style · both romance
Popcorn FlickMovies like thisHair Wolf (2018)
The staff of a black hair salon fend off a strange new monster: white women intent on sucking the lifeblood from black culture.
Why it matches: Similar story and style · both comedy
Like Crossing Hennessy and something else?
Blend two favourites and we’ll find the films in between.
Frequently asked questions
What are the best movies like Crossing Hennessy?
The closest matches to Crossing Hennessy are Chasing Papi (2003), The Prince & Me 4: The Elephant Adventure (2010) and Crossing Delancey (1988). Below are 27 more, each with the reason it matches.
What should I watch after Crossing Hennessy?
Start with Chasing Papi (2003), the closest match to Crossing Hennessy.
What is the highest-rated movie like Crossing Hennessy?
The Wrong Paris (2025), rated 6.7/10 by 359 TMDB users.
What is the newest movie like Crossing Hennessy?
Yoh! Bestie (2026) is the most recent release on this list.
How are movies similar to Crossing Hennessy chosen?
First come films that Trakt’s viewers watch alongside Crossing Hennessy, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.