Movies like Chennai 2 Singapore (2017)
The best movies like Chennai 2 Singapore (2017) are An Unexpected Christmas (2021), Irreplaceable You (2018) and You Will Meet a Tall Dark Stranger (2010). If Chennai 2 Singapore hooked you with its drama and comedy, these 30 similar films are what to watch next, and every pick says why it matches.
Quick picks
- Highest ratedTo All the Boys: Always and Forever (2021)7.5/10 from 2,107 votes
- NewestVishwanath & Sons (2026)Released 2026
- In TamilVishwanath & Sons (2026)Also in Tamil
An Unexpected Christmas (2021)
Jamie hasn’t told his family that he and his now ex-girlfriend Emily broke up. After an inopportune run-in with Emily at the train station in his hometown, Jamie convinces her to pretend they’re still a couple to avoid ruining Christmas for his family.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisIrreplaceable You (2018)
A stunning cancer diagnosis spurs Abbie to seek a future girlfriend for fiancé and childhood sweetheart Sam, who's clueless when it comes to dating.
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies like thisYou Will Meet a Tall Dark Stranger (2010)
Two married couples find only trouble and heartache as their complicated lives unfold. After 40 years of marriage, Alfie leaves his wife to pursue what he thinks is happiness with a call girl. His wife, Helena, reeling from abandonment, decides to follow the advice of a psychic. Sally, the daughter of Alfie and Helena, is unhappy in her marriage and develops a crush on her boss, while her husband, Roy, falls for a woman engaged to be married.
Why it matches: Recommended by TMDB viewers · both comedy & drama
SnoozefestMovies like thisVishwanath & Sons (2026)
A celebrated Olympian shooter travels to America looking for a donor to help his sick child — but unexpected romance complicates his search.
Why it matches: Recommended by TMDB viewers · both drama & romance
Worth the HypeMovies like thisJolly Good Christmas (2022)
David is an American architect who relocates across the pond to take up a job at a prestigious London firm. As the clock counts down to Christmas Day, David is running out of time to buy his girlfriend – who also happens to be his boss’s daughter – a thoughtful present so he resorts to buying her a somewhat uninspired gift card.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisTo All the Boys: Always and Forever (2021)
Senior year of high school takes center stage as Lara Jean returns from a family trip to Korea and considers her college plans — with and without Peter.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Worth the HypeMovies like thisPicture Perfect (1997)
A young advertising executive's life becomes increasingly complicated when, in order to impress her boss, she pretends to be engaged to a man she has just met.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisThiruchitrambalam (2022)
A guy-next-door tries to find romance in his life while also dealing with his personal problems. How long will it be before he realises what he is looking for is right next to him?
Why it matches: Recommended by TMDB viewers · both comedy & drama
Worth the HypeMovies 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 thisHitch (2005)
Dating coach Alex 'Hitch' Hitchens mentors a bumbling client, Albert, who hopes to win the heart of the glamorous Allegra Cole. While Albert makes progress, Hitch faces his own romantic setbacks when proven techniques fail to work on Sara Melas, a tabloid reporter digging for dirt on Allegra Cole's love life. When Sara discovers Hitch's connection to Albert – now Allegra's boyfriend – it threatens to destroy both relationships.
Why it matches: Recommended by TMDB viewers · both comedy & drama
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 thisThe Lost Husband (2020)
Trying to put her life back together after the death of her husband, Libby and her children move to her estranged Aunt's goat farm in central Texas.
Why it matches: Recommended by TMDB viewers · both drama & 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 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 thisMy Brilliant Career (1979)
A young woman who is determined to maintain her independence finds herself at odds with her family who wants her to tame her wild side and get married.
Why it matches: Recommended by TMDB viewers · both drama & romance
Popcorn FlickMovies like thisCrazy Rich Asians (2018)
An American-born Chinese economics professor accompanies her boyfriend to Singapore for his best friend's wedding, only to get thrust into the lives of Asia's rich and famous.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisWhat a Way to Go! (1964)
A four-time widow discusses her four marriages, in which all of her husbands became incredibly rich and died prematurely because of their drive to be rich.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Worth the HypeMovies like thisFlamingo Road (1949)
A stranded carnival dancer takes on a corrupt political boss when she marries into small-town society.
Why it matches: Recommended by TMDB viewers · both drama & romance
Worth the HypeMovies like thisChristmas at the Drive-In (2022)
Sadie Walker is starting over in her hometown of Chesterfield, New York, following a series of major life disruptions that include leaving her law practice after losing her biggest case and no longer being engaged.
Why it matches: Recommended by TMDB viewers · both comedy & romance
SnoozefestMovies like thisA Valentine's Match (2020)
Fired from her job as a reality TV host, Natalie returns home for Valentine's Day, only to find herself running the town festival's auction with her ex-fiancé thanks to two scheming mothers.
Why it matches: Recommended by TMDB viewers · both romance & drama
Worth the HypeMovies like thisTorremolinos 73 (2003)
Set in 1973 Spain, a struggling encyclopedia salesman and his wife take advantage of an offer to make adult films. The act turns him into an aspring legit filmmaker and her into an international sex symbol.
Why it matches: Similar story and style · both comedy & drama
Popcorn FlickMovies like thisThe Beautiful Confusion (2025)
Through repeated takes and mounting tension, a divided cast and crew on an indie film set slowly learn to work together through conflict and vulnerability.
Why it matches: Similar story and style · both drama & comedy
Beware of a Holy Whore (1971)
Film director Jeff and his lead actor are taking their time getting to set. In their absence, the crew lack a purposeful way to spend their time waiting, so they drink heavily. However, as booze is downed and frustration sets in, morale hits rock bottom.
Why it matches: Similar story and style · both drama & comedy
Popcorn FlickMovies like thisAlex in Wonderland (1970)
Bohemian Alex Morrison has just finished directing his first feature length movie. In its previews, the movie is considered a critical, artistic and surefire commercial success. As such, Alex seemingly has his choice of what his next project will be. As he makes the rounds both in the Hollywood community and European movie centers for ideas, he fantasizes about movie scenarios of those everyday situations he is in.
Why it matches: Similar story and style · both comedy & drama
Alistair1918 (2015)
A social work grad student’s film project on L.A. homelessness becomes something quite other when she and her friends encounter a man claiming to be from another time and place.
Why it matches: Similar story and style · both drama
Mayouya, un film africain sans budget (2022)
Frédérique has obtained a firm commitment for the financing of her film on excision. At the last moment, however, the bank withdrew. Instead, the director asks her to become one of his many mistresses. The young woman decides to teach him a good lesson...
Why it matches: Similar story and style · both comedy
The Graveyard Feeder (2013)
Cemetery caretaker Burke Sawyer and his deceased father, Pop Sawyer, team up to investigate a creature feeding on the dead underground.
Why it matches: Similar story and style · both comedy
Tea Leaves & Lilies (2023)
« Having just lost her mother, Li Jing honors her dearly departed as best she can by following her way of life only to be troubled by the sudden reappearance of her absentee father. In this moment of loss and uncertainty, Li Jing attempts to heal her past wounds through the spiritual teachings of tea... »
Why it matches: Similar story and style · both drama
Orgazmo (1998)
A devout Mormon living in L.A. becomes a pornographic actor after his martial arts moves impress a big-time director.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisA Cock and Bull Story (2005)
Steve Coogan, an arrogant actor with low self-esteem and a complicated love life, is playing the eponymous role in an adaptation of "The Life and Opinions of Tristram Shandy, Gentleman" being filmed at a stately home. He constantly spars with actor Rob Brydon, who is playing Uncle Toby and believes his role to be of equal importance to Coogan's.
Why it matches: Similar story and style · both comedy
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Frequently asked questions
What are the best movies like Chennai 2 Singapore?
The closest matches to Chennai 2 Singapore are An Unexpected Christmas (2021), Irreplaceable You (2018) and You Will Meet a Tall Dark Stranger (2010). Below are 27 more, each with the reason it matches.
What should I watch after Chennai 2 Singapore?
Start with An Unexpected Christmas (2021), the closest match to Chennai 2 Singapore.
What is the highest-rated movie like Chennai 2 Singapore?
To All the Boys: Always and Forever (2021), rated 7.5/10 by 2,107 TMDB users.
What is the newest movie like Chennai 2 Singapore?
Vishwanath & Sons (2026) is the most recent release on this list.
Are there Tamil movies like Chennai 2 Singapore?
Yes: Vishwanath & Sons (2026) and Thiruchitrambalam (2022).
How are movies similar to Chennai 2 Singapore chosen?
First come films that Trakt’s viewers watch alongside Chennai 2 Singapore, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.