Dynamic Watchlist Hub: May 18, 2026

10 Best Movies Like I'm Trying to Impress You

If you loved I'm Trying to Impress You, we've curated the perfect watchlist for you based on shared genres, themes, and directorial style.

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Expert Review & Ratings

See our full critical analysis and audience score for I'm Trying to Impress You.

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#1
My Sassy Girl

My Sassy Girl

2008★ 6.7

Why watch this? A perfect follow-up to I'm Trying to Impress You for fans of Romance & Comedy. It captures a similar light-hearted atmosphere.

A guy has his life planned out until he is wooed, groomed and then dumped by an elusive woman....

#2
Playing It Cool

Playing It Cool

2014★ 5.9

Why watch this? A perfect follow-up to I'm Trying to Impress You for fans of Romance & Comedy. It captures a similar light-hearted atmosphere.

A young man meets and instantly falls in love with an engaged woman....

#3
Love Is in the Air

Love Is in the Air

2023★ 6.2

Why watch this? A perfect follow-up to I'm Trying to Impress You for fans of Romance & Comedy. It captures a similar light-hearted atmosphere.

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....

#4
Relationship Goals

Relationship Goals

2026★ 5.8

Why watch this? A perfect follow-up to I'm Trying to Impress You for fans of Romance & Comedy. It captures a similar light-hearted atmosphere.

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 chemis...

#5
I'm No Angel

I'm No Angel

1933★ 6.4

Why watch this? A perfect follow-up to I'm Trying to Impress You for fans of Romance & Comedy. It captures a similar light-hearted atmosphere.

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! ...

#6
The Other End of the Line

The Other End of the Line

2007★ 6.4

Why watch this? A perfect follow-up to I'm Trying to Impress You for fans of Romance & Comedy. It captures a similar light-hearted atmosphere.

An employee at an Indian call-center travels to San Francisco to be with a guy she falls for over the phone....

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