Dynamic Watchlist Hub: May 09, 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
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...

#2
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 ...

#3
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...

#4
A Perfect Getaway

A Perfect Getaway

2009★ 6.3

Why watch this? A perfect follow-up to Flirting with Forty for fans of Thriller. It captures a similar compelling atmosphere.

For their honeymoon, newlyweds Cliff and Cydney head to the tropical islands of Hawaii. While journeying through the paradisaical countryside the couple encounters Kale and Cleo, t...

#5
Stuck in Love

Stuck in Love

2013★ 7.4

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

An acclaimed writer, his ex-wife, and their teenaged children come to terms with the complexities of love in all its forms over the course of one tumultuous year....

#6
Good Luck to You, Leo Grande

Good Luck to You, Leo Grande

2022★ 7.0

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

Nancy Stokes, a retired schoolteacher, is pretty sure she has never had good sex. Now that her husband has died, she is determined to take a tour of sexual vistas that until now sh...

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