Dynamic Watchlist Hub: Apr 18, 2026

10 Best Movies Like Trifling with Fate

If you loved Trifling with Fate, 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 Trifling with Fate.

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#1
Coyote Ugly

Coyote Ugly

2000★ 6.3

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

Graced with a velvet voice, 21-year-old Violet Sanford heads to New York to pursue her dream of becoming a songwriter only to find her aspirations sidelined by the accolades and no...

#2
Romance & Cigarettes

Romance & Cigarettes

2005★ 6.0

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

Ironworker Nick lives with his wife, Kitty, and three daughters. When he meets a significantly younger woman, Tula, he starts an affair with her, much to the chagrin of his wife, a...

#3
The Incredible Jessica James

The Incredible Jessica James

2017★ 6.2

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

Burned by a bad breakup, a struggling New York City playwright makes an unlikely connection with a divorced app designer she meets on a blind date....

#4
Which Brings Me to You

Which Brings Me to You

2023★ 6.2

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

Two romantic burnouts, Jane and Will, are immediately drawn to each other at a mutual friend’s wedding. After a disastrous hookup in the coatroom, the two spend the next 24 hours t...

#5
Strictly Sexual

Strictly Sexual

2008★ 6.1

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

Two successful women, sick and tired of dating and relationships, decide to keep two young men in their pool house for strictly sexual purposes....

#6
(Untitled)

(Untitled)

2009★ 6.4

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

A fashionable contemporary art gallerist in Chelsea, New York falls for a brooding new music composer in this comic satire of the state of contemporary art....

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