Movies like I'm Trying to Impress You (2016)
The best movies like I'm Trying to Impress You (2016) are Dinner in America (2022), I'm No Angel (1933) and My Sassy Girl (2008). If I'm Trying to Impress You hooked you with its romance and comedy, these 30 similar films are what to watch next, and every pick says why it matches.
I'm Trying to Impress You
Quick picks
- Highest ratedThe Apartment (1960)8.2/10 from 2,848 votes
- NewestOne Night Only (2026)Released 2026
Dinner in America (2022)
An on-the-lam punk rocker and a young woman obsessed with a local band go on an unexpected and epic journey together through the decaying suburbs of the American Midwest.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Worth the HypeMovies like thisI'm No Angel (1933)
Bold performer Tira works as dancing beauty and lion tamer at a fair. Out of an urgent financial need, she agrees to a risky new number: she'll put her head into the lion's mouth! With this attraction, the circus makes it to New York and Tira can pursue her dearest occupation — flirting with rich men and accepting expensive presents.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies 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 thisPlaying It Cool (2014)
A young man meets and instantly falls in love with an engaged woman.
Why it matches: Recommended by TMDB viewers · both comedy & romance
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 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 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 thisOne Night Only (2026)
Two love-starved strangers crash into each other on the one night of the year when single people are allowed to have sex.
Why it matches: Recommended by TMDB viewers · both romance & comedy
Popcorn FlickMovies like thisTromeo & Juliet (1996)
All the body-piercing, kinky sex, and car crashes that Shakespeare wanted but never had! Join Tromeo and Juliet as they travel through Manhattan's underground in search of climactic love, violence and the American Way.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisThe Other End of the Line (2007)
An employee at an Indian call-center travels to San Francisco to be with a guy she falls for over the phone.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisWe Broke Up (2021)
Lori and Doug break up right before Lori's sister's wedding and decide to pretend they're still together for the weekend as to not disrupt the fun.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisValentine's Day (2010)
Intertwining couples and singles in Los Angeles break-up and make-up based on the pressures and expectations of Valentine's Day.
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 thisThat Touch of Mink (1962)
Cathy Timberlake is en route to a job interview when a car transporting businessman Philip Shayne covers her in mud. He sends his assistant, Roger, to apologize, but upon meeting Cathy, Roger knows that she would be a suitable match for his boss. Despite their mutual attraction, Cathy and Philip want different things. Philip wants a fling, while Cathy wants a marriage. As they travel to exotic locales, their differing motivations are put to the test.
Why it matches: Recommended by TMDB viewers · both comedy & romance
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 thisThe Smiling Lieutenant (1931)
An amorous lieutenant is forced to marry a socially awkward princess, though he tries to keep his violin-playing girlfriend on the side.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisPlatinum Blonde (1931)
Ann Schuyler is an upper-crust socialite who bullies her reporter husband into conforming to her highfalutin ways. The husband chafes at the confinement of high society, though, and yearns for a creative outlet. He decides to write a play and collaborates with a fellow reporter.
Why it matches: Recommended by TMDB viewers · both comedy & romance
Popcorn FlickMovies like thisSundown (2016)
High school seniors Logan and Blake prepare for an epic Spring Break as they travel to the beautiful and exotic Mexican beach resort of Puerto Vallarta hoping to hook up with their high school crushes. Surrounded by hot girls in teeny bikinis, the guys are truly in heaven. After meeting at a club, Logan falls for a mysterious local beauty named Gaby but then realizes the next morning, when his grandfather’s Rolex watch is missing, that she was after more than just his heart.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies 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 thisThe List (2023)
After her fiance sleeps with a celebrity on his free pass list, Abby Meyers, with nothing but five names and a fantasy shared by millions, sets out for Los Angeles to sleep with someone from hers.
Why it matches: Recommended by TMDB viewers · both romance & comedy
SnoozefestMovies like thisBewitched (2021)
It's more dificult to love than to be bewitched. The film has as it's central theme the loving separation, but the consequences of this separation are attributed to occult forces that throwing the protagonist in the world of Afro-Brazilian mystical religions.
Why it matches: Similar story and style · both comedy & romance
Garden State (2004)
Andrew returns to his hometown for his mother’s funeral, a journey that reconnects him with old friends. The trip coincides with his decision to stop taking his powerful antidepressants. A chance meeting with Sam—a girl also struggling with various maladies—opens up the possibility of rekindling emotional connections, confronting his psychologist father, and perhaps beginning a new life.
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 thisChocolat (2000)
In the winter of 1959, a single mother and her young daughter arrive in a rural French town, where they open an unusual chocolate shop that disrupts the moral fiber of the strictly Catholic townsfolk and mayor.
Why it matches: Similar story and style · both comedy & romance
Worth the HypeMovies like thisNotting Hill (1999)
London bookstore owner William Thacker's quiet life turns upside down when a chance encounter with famous actress Anna Scott sparks an unlikely romance challenged by their vastly different worlds.
Why it matches: Similar story and style · both romance & comedy
Worth the HypeMovies like thisRoman Holiday (1953)
Overwhelmed by her suffocating schedule, touring European princess Ann takes off for a night while in Rome. When a sedative she took from her doctor kicks in, however, she falls asleep on a park bench and is found by an American reporter, Joe Bradley, who takes her back to his apartment for safety. At work the next morning, Joe finds out Ann's regal identity and bets his editor he can get exclusive interview with her, but romance soon gets in the way.
Why it matches: Similar story and style · both romance & comedy
Absolute CinemaMovies like thisThe General (1926)
During America’s Civil War, Union spies steal engineer Johnnie Gray's beloved locomotive, 'The General'—with Johnnie's lady love aboard an attached boxcar—and he single-handedly must do all in his power to both get The General back and to rescue Annabelle.
Why it matches: Similar story and style · both comedy & romance
Absolute CinemaMovies like thisLa Dolce Vita (1960)
Episodic journey of journalist Marcello who struggles to find his place in the world, torn between the allure of Rome's elite social scene and the stifling domesticity offered by his girlfriend, all the while searching for a way to become a serious writer.
Why it matches: Similar story and style · both comedy
Absolute CinemaMovies like thisHuman Nature (2001)
Obsessive scientist Nathan and his lover, the naturalist Lila, discover Puff: a man born and raised in the wild. As Nathan trains the wild man in the civilized ways of the world, Lila fights to preserve the man’s natural state. In the power struggle that ensues, an unusual love triangle emerges.
Why it matches: Similar story and style · both comedy
Popcorn FlickMovies like thisLeaving Las Vegas (1995)
Ben Sanderson, an alcoholic Hollywood screenwriter who lost everything because of his drinking, arrives in Las Vegas to drink himself to death. There, he meets and forms an uneasy friendship and non-interference pact with prostitute Sera.
Why it matches: Similar story and style · both romance
Worth the HypeMovies like this
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Frequently asked questions
What are the best movies like I'm Trying to Impress You?
The closest matches to I'm Trying to Impress You are Dinner in America (2022), I'm No Angel (1933) and My Sassy Girl (2008). Below are 27 more, each with the reason it matches.
What should I watch after I'm Trying to Impress You?
Start with Dinner in America (2022), the closest match to I'm Trying to Impress You.
What is the highest-rated movie like I'm Trying to Impress You?
The Apartment (1960), rated 8.2/10 by 2,848 TMDB users.
What is the newest movie like I'm Trying to Impress You?
One Night Only (2026) is the most recent release on this list.
Are there English movies like I'm Trying to Impress You?
Yes: Dinner in America (2022), I'm No Angel (1933) and My Sassy Girl (2008).
How are movies similar to I'm Trying to Impress You chosen?
First come films that Trakt’s viewers watch alongside I'm Trying to Impress You, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.