Dynamic Watchlist Hub: Apr 16, 2026

10 Best Movies Like Sleepless

If you loved Sleepless, 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 Sleepless.

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#1
Little Italy

Little Italy

2018★ 6.6

Why watch this? A perfect follow-up to Sleepless for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

Former childhood pals Leo and Nikki are attracted to each other as adults—but will their feuding parents' rival pizzerias put a chill on their sizzling romance?...

#2
A Nice Girl Like You

A Nice Girl Like You

2020★ 5.8

Why watch this? A perfect follow-up to Sleepless for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

Lucy Neal is thrown for a loop when she is accused of being too inhibited by her ex-boyfriend. In an effort to prove him wrong, Lucy creates a rather wild to-do list that sends her...

#3
Desperados

Desperados

2020★ 6.0

Why watch this? A perfect follow-up to Sleepless for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

A panicked young woman and her two best friends fly to Mexico to delete a ranting email she sent to her new boyfriend. On arrival, they run into her former beau, who soon gets caug...

#4
Players

Players

2024★ 6.1

Why watch this? A perfect follow-up to Sleepless for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

New York sportswriter Mack has spent years devising successful hook-up "plays" with her friends, but when she unexpectedly falls for one of her targets, she must learn what it take...

#5
I Love You Again

I Love You Again

1940★ 7.2

Why watch this? A perfect follow-up to Sleepless for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

Boring businessman Larry Wilson recovers from amnesia and discovers he's really a con man...and loves his soon-to-be-ex wife....

#6
¿Quieres ser mi hijo?

¿Quieres ser mi hijo?

2023★ 8.5

Why watch this? A perfect follow-up to Sleepless for fans of Comedy & Romance. It captures a similar light-hearted atmosphere.

Lu, 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 ...

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