Dynamic Watchlist Hub: Apr 19, 2026

10 Best Movies Like Flirting with Forty

If you loved Flirting with Forty, 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 Flirting with Forty.

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#1
The Four Seasons

The Four Seasons

1981★ 6.2

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

Three middle-aged wealthy couples take vacations together in Spring, Summer, Autumn and Winter. Along the way we are treated to mid-life, marital, parental and other crises....

#2
Just Go with It

Just Go with It

2011★ 6.7

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

While romancing Palmer, a much younger schoolteacher, plastic surgeon Danny Maccabee enlists his loyal assistant Katherine to pretend to be his soon to be ex-wife, in order to cove...

#3
Forgetting Sarah Marshall

Forgetting Sarah Marshall

2008★ 6.5

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

When actress Sarah Marshall dumps aspiring musician Peter Bretter for rock star Aldous Snow, Peter's world comes crashing down. His best friend Brian suggests that Peter should get...

#4
Venus

Venus

2006★ 6.6

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

Maurice is an aging veteran actor who becomes taken with Jessie, the grandniece of his closest friend. When Maurice tries to soften the petulant and provincial young girl with the ...

#5
Summer of '42

Summer of '42

1971★ 6.7

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

Over the summer of 1942 on Nantucket Island, three friends -- Hermie, Oscy and Benjie -- are more concerned with getting laid than anything else. Hermie falls in love with the marr...

#6
Donovan's Reef

Donovan's Reef

1963★ 6.2

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

After her great aunt's death, a high-society woman arrives on a Hawaiian island in search of the heir - the father she has never met....

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