Movies like Dating the Enemy (1996)
The best movies like Dating the Enemy (1996) are The Secret Life of Walter Mitty (1947), Love Potion No. 9 (1992) and Two of a Kind (1983). If Dating the Enemy hooked you with its comedy and fantasy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedFrida (2002)7.4/10 from 2,236 votes
- NewestYoh! Bestie (2026)Released 2026
The Secret Life of Walter Mitty (1947)
Walter Mitty, a daydreaming writer with an overprotective mother, likes to imagine that he is a hero who experiences fantastic adventures. His dream becomes reality when he accidentally meets a mysterious woman who hands him a little black book. According to her, it contains the locations of the Dutch crown jewels hidden since World War II. Soon, Mitty finds himself in the middle of a confusing conspiracy, where he has difficulty differentiating between fact and fiction.
Why it matches: Recommended by TMDB viewers · both comedy & fantasy
Popcorn FlickMovies like thisLove Potion No. 9 (1992)
Unlucky in love, chemist Paul Matthews visits gypsy Madame Rosa for help. Quickly realizing he is a hopeless nerd, she gifts him with Love Potion No. 8, which makes anyone who wears it irresistible to the opposite sex for four hours. Paul and animal psychologist coworker Diane Farrow decide to test it on themselves. The awkward pair suddenly find themselves alluring to anyone they approach, but soon realize they are most attracted to each other.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisTwo of a Kind (1983)
God has had enough of the bad behavior and attitude of humankind, and has decided to start it all over. It is up to a struggling inventor and a bank teller, both with very amateur criminal minds, to save the world by falling in love.
Why it matches: Recommended by TMDB viewers · both fantasy & comedy
Popcorn FlickMovies like thisKiss Me Goodbye (1982)
Not until three years after the death of her husband Jolly, Kay dares to move back into their former home, persuaded by her new fiancée Rupert. But soon her worst expectations come true, when not only her old memories haunt her, but also Jolly's ghost, who doesn't approve of her new mate. Invisible to anyone but Kay, he tries to prevent the wedding.
Why it matches: Recommended by TMDB viewers · both comedy & fantasy
SnoozefestMovies like thisDate with an Angel (1987)
Aspiring composer Jim Sanders is engaged to spoiled rich girl Patty. But the morning after his bachelor party, Jim wakes up to discover a beautiful, broken-winged angel in his pool. When everyone finds out about his heavenly houseguest, Jim must cope with a dangerously jealous fiancée, an exploitive future father-in-law and a group of buddies with an outrageous business plan!
Why it matches: Recommended by TMDB viewers · both comedy & fantasy
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 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 thisChasing 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 thisThis Little Love of Mine (2021)
Laura Price is a successful San Francisco lawyer on the cusp of promotion – a far cry from her childhood growing up on a tropical island with best friends Chip and Gem. When the firm’s biggest client – Chip’s grandfather – asks Laura to travel to the island and deliver a contract to make Chip his heir, she leaves behind her practice and fiancé Owen to convince her childhood friend to sign a contract that will make him a billionaire.
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 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 thisGirl on a Bicycle (2013)
Paolo, an Italian tour bus driver living in Paris, has just summoned up the courage to propose marriage to his German girlfriend Greta. However, a chance encounter with a French woman on a bicycle the very next day turns Paolo's life upside down.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies 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 thisHer Pen Pal (2021)
Event planner Victoria can’t wait to attend –- and plan –- her best friend’s wedding in Paris. But when she finds out her ex is bringing a date, Victoria reconnects with her French childhood pen pal.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisMy Favorite Wedding (2017)
Potential Northwestern fellow Tess Harper lasers through her best friend's wedding planning like the star doctor she hopes to soon become. In fact, Tess puzzles through any problem - provided it's not her own. When she meets divorce lawyer and groom's best friend, Michael, Tess maneuvers around him like a gurney in the emergency room until she discovers this best man has a few moves of his own.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisLove Jacked (2018)
Maya, a headstrong 28-year-old with artistic ambitions – a strong contrast to what her father Ed wants: a dutiful daughter to run the family store. Ed is shocked when Maya takes her assertions of independence a step further and decides to travel to Africa for inspiration and returns with a fiancé who is not quite what he seems.
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 thisAll Things Valentine (2016)
Avery, a blogger with a string of disappointing Valentine’s Days, is ready to give up on love when she meets handsome veterinarian Brenden. When Avery finds out Brenden blames his recent break up on her blog and is the one leaving her angry comments, she begins to question whether the bond they’ve began to build is a true love story or yesterday’s news.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies 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 Right Kind of Wrong (2013)
A stubborn idealist spies a bride on her way to her wedding and immediately falls in love with her.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisTaste of Love (2016)
After an ambiguous Snapchat video featuring Bilel and Adil, rumors start spreading about the two friends. To save their reputation, each of them tries to find a girlfriend. Their hunt for a date doesn’t quite go as expected.
Why it matches: Similar story and style · both romance & comedy
The Holiday (2006)
Two women, one American and one British, swap homes at Christmastime following bad breakups. Each woman finds romance with a local man but realizes that the imminent return home may end the relationship.
Why it matches: Similar story and style · both comedy & romance
Worth the HypeMovies like thisAll for Love (2017)
When a romance novelist is teamed with a Navy SEAL as research for her book, by a mandate from her publisher, she is less than thrilled and he is more than honest. However, as she works with the SEAL, she has a change of heart and learns to look at her life and writing with a different point of view.
Why it matches: Similar story and style · both romance & comedy
Popcorn FlickMovies like thisMichael (1996)
Tabloid reporters are sent by their editor to investigate after the paper recieves a letter from a woman claiming an angel is living with her.
Why it matches: Similar story and style · both comedy & fantasy
SnoozefestMovies like thisMostly Martha (2001)
Martha is a single woman who lives for one passion: cooking. The head chef at a chic restaurant, Martha has no time for anything - or anyone - else. But Martha's solitary life is shaken when a fateful accident brings her sister's eight-year-old daughter, Lina, to her doorstep.
Why it matches: Similar story and style · both comedy & romance
Popcorn FlickMovies like thisTMNT (2007)
After the defeat of their old arch nemesis, The Shredder, the Turtles have grown apart as a family. Struggling to keep them together, their rat sensei, Splinter, becomes worried when strange things begin to brew in New York City.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisAmsterdam to Anatolia (2019)
Elissa's life takes a turn when she meets a mysterious man in her English class and she has to quickly decide between her family and him- and going from family-life to a life on the run is a wild choice to everyone but her.
Why it matches: Similar story and style · both romance
Words with Gods (2014)
The first of four installments in the groundbreaking Heartbeat of the World anthology film series. Comprised of several short films by some of the world's most exciting directors, Words with Gods follows the theme of religion - specifically as it relates to an individual's relationship with his/her god or gods...or the lack thereof. In Words with Gods, each director recounts a narrative centered around human fragility, as well as environmental and cultural crises involving specific religions with which each has a personal relationship; including early Aboriginal Spirituality, Umbanda, Buddhism, the Abrahamic faiths, Hinduism, and Atheism. An animated sequence by Mexican animator Maribel Martinez is woven through each of the film segments, with each segment narratively connected as a feature-length film.
Why it matches: Similar story and style · both comedy
Frida (2002)
A biography of artist Frida Kahlo, who channeled the pain of a crippling injury and her tempestuous marriage into her work.
Why it matches: Similar story and style · both romance
Worth the HypeMovies like thisF Is for Friendship (2017)
Emily decides to air the skeletons in her closet and brave the scrutiny of a catty dinner party to win back her name.
Why it matches: Similar story and style · both comedy
Like Dating the Enemy and something else?
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Frequently asked questions
What are the best movies like Dating the Enemy?
The closest matches to Dating the Enemy are The Secret Life of Walter Mitty (1947), Love Potion No. 9 (1992) and Two of a Kind (1983). Below are 27 more, each with the reason it matches.
What should I watch after Dating the Enemy?
Start with The Secret Life of Walter Mitty (1947), the closest match to Dating the Enemy.
What is the highest-rated movie like Dating the Enemy?
Frida (2002), rated 7.4/10 by 2,236 TMDB users.
What is the newest movie like Dating the Enemy?
Yoh! Bestie (2026) is the most recent release on this list.
Are there English movies like Dating the Enemy?
Yes: The Secret Life of Walter Mitty (1947), Love Potion No. 9 (1992) and Two of a Kind (1983).
How are movies similar to Dating the Enemy chosen?
First come films that Trakt’s viewers watch alongside Dating the Enemy, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.