Movies Like I'm Trying to Impress You
If you liked I'm Trying to Impress You (2016), a romance and comedy movie directed by Taylor Phillips, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.
- 1
I'm No Angel (1933)
★ 6.4/10Also comedy and romanceBold 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…
- 2
Dinner in America (2022)
★ 7.8/10Also romance and comedyAn 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.
- 3
Playing It Cool (2014)
★ 5.9/10Also comedy and romanceA young man meets and instantly falls in love with an engaged woman.
- 4
My Sassy Girl (2008)
★ 6.8/10Also comedy and romanceA guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman.
- 5
Love Is in the Air (2023)
★ 6.2/10Also romance and comedyA fiercely independent pilot fighting to keep her family business afloat starts to fall for the man sent by corporate to ground her operation forever.
- 6
Relationship Goals (2026)
★ 6.4/10Also romance and comedyWhen 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…
- 7
One Night Only (2026)
★ 6.4/10Also romance and comedyTwo love-starved strangers crash into each other on the one night of the year when single people are allowed to have sex.
- 8
The Other End of the Line (2007)
★ 6.5/10Also comedy and romanceAn employee at an Indian call-center travels to San Francisco to be with a guy she falls for over the phone.
- 9
Valentine's Day (2010)
★ 5.9/10Also comedy and romanceIntertwining couples and singles in Los Angeles break-up and make-up based on the pressures and expectations of Valentine's Day.
- 10
The Wrong Paris (2025)
★ 6.7/10Also romance and comedyDawn 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.
- 11
That Touch of Mink (1962)
★ 6.5/10Also comedy and romanceCathy 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…
- 12
Yoh! Bestie (2026)
★ 6.2/10Also romance and comedyThando 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.
- 13
We Broke Up (2021)
★ 5.9/10Also romance and comedyLori 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.
- 14
I Love You Again (1940)
★ 7.2/10Also comedy and romanceBoring businessman Larry Wilson recovers from amnesia and discovers he's really a con man...and loves his soon-to-be-ex wife.
- 15
Your Christmas or Mine? (2022)
★ 6.4/10Also comedy and romanceStudents Hayley and James are young and in love. After saying goodbye for Christmas at a London train station, they both make the same mad split-second decision to swap trains and surprise each other. Passing each…
- 16
Sex Appeal (2022)
★ 6.6/10Also comedy and romanceAvery, a teenager with a tendency towards perfectionism, enlists her friend Larson to help her prepare for her first time with her long-distance boyfriend.
- 17
Send Me No Flowers (1964)
★ 6.8/10Also comedy and romanceWhen a hypochondriac assumes that he is dying, he makes an elaborate plan to ensure his wife's happiness. However, trouble ensues when she misunderstands his intentions.
- 18
There's Something About Mary (1998)
★ 6.6/10Also romance and comedyFor Ted, prom night went about as bad as it’s possible for any night to go. Thirteen years later, he finally gets another chance with his old prom date, only to run up against other suitors including the sleazy…
- 19
Someone Great (2019)
★ 6.4/10Also comedy and romanceAn 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…
- 20
¿Quieres ser mi hijo? (2023)
★ 8.4/10Also comedy and romanceLu, 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.