Dynamic Watchlist Hub: Jan 31, 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
Trying to Get Good: The Jazz Odyssey of Jack Sheldon

Trying to Get Good: The Jazz Odyssey of Jack Sheldon

2008★ 4.5

Why watch this? A perfect follow-up to I'm Trying to Impress You for fans of Documentary. It captures a similar compelling atmosphere.

Trumpeter and vocalist Jack Sheldon, best known to younger viewers for Schoolhouse Rock, tries to "get good." Recovering from many years of substance abuse and overcoming personal ...

#2
Strange Object

Strange Object

2020★ 6.0

Why watch this? A perfect follow-up to I'm Trying to Impress You for fans of Documentary. It captures a similar compelling atmosphere.

An archival investigation into the imperial image-making of the RAF ‘Z Unit’, which determined the destruction of human, animal and cultural life across Somaliland, as well as Afri...

#3
Florence Fight Club

Florence Fight Club

2015★ 7.4

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

Intertwined stories from the gladiator/athletes participating to the Calcio Storico Fiorentino yearly championship....

#4
The Courtyard of Memories

The Courtyard of Memories

2025★ 5.4

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

Vanessa inherits an old Portuguese Revue theatre after the death of a distant aunt. Her agent, Tozé Leal, tries to convince her to sell it, but she decides to restore it to its for...

#5
Dune

Dune

2020★ 7.4

Why watch this? A perfect follow-up to I'm Trying to Impress You for fans of Animation. It captures a similar compelling atmosphere.

Sounds as witnesses. They blurr into memories, half-dreams, it is undecided if they are real or not. A fluctuation between imagination and reality....

#6
MAD

MAD

2021★ 5.6

Why watch this? A perfect follow-up to I'm Trying to Impress You for fans of Drama. It captures a similar emotionally gripping atmosphere.

Have you ever felt lonely in a Relationship..., Marriage or Live_In , doesn't matter, when you can't share your feelings with your companion, it is like travelling to an unknown de...