Dynamic Watchlist Hub: Apr 14, 2026

10 Best Movies Like Courting Trouble

If you loved Courting Trouble, 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 Courting Trouble.

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#1
Easy Money

Easy Money

1983★ 6.0

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

To inherit his mother-in-law's colossal fortune, a hard living gambling addict must change his unhealthy ways before it gets the best of him....

#2
Watching the Detectives

Watching the Detectives

2007★ 6.3

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

Neil, a self-proclaimed film geek and owner of Gumshoe video, has always been content to live vicariously through his favorite films noir. But when he meets Violet, a real-life fem...

#3
About Alex

About Alex

2014★ 6.1

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

When a group of old college friends reunite over a long weekend after one of them attempts suicide, old crushes and resentments shine light on their life decisions, and ultimately ...

#4
Sextuplets

Sextuplets

2019★ 6.2

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

Father-to-be Alan is shocked to learn that he was born a sextuplet. With his newfound brother Russell riding shotgun, the duo sets out on a hilarious journey to reunite with their ...

#5
I Love My Dad

I Love My Dad

2022★ 5.9

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

A hopelessly estranged father catfishes his son in an attempt to reconnect....

#6
Hooking Up

Hooking Up

2020★ 6.3

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

Bailey and Darla embark upon a misguided and mutually deceitful form of therapy, one in which they must drive across the country, re-enacting Darla's colorful history as a sex addi...

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