Movies Like Flirting with Forty

Ranked by shared directors, cast, themes, genre, and era — not just generic recommendations.

Fallen

2006·1h 24m·★ 6.4·Mikael Salomon

2 shared crewDir. Mikael SalomonDP: Jon Joffin

A Glimpse of Hell

2001·1h 25m·★ 6.1·Mikael Salomon

2 shared crewDir. Mikael SalomonDP: Jon Joffin

Just Go with It

2011·1h 57m·★ 6.4·Dennis Dugan

Themes: divorced, hawaiiFans also likedComedy & Romance

Blue Crush

2002·1h 44m·★ 5.7·John Stockwell

Themes: surfing, hawaiiFans also likedRomance & Drama

Forgetting Sarah Marshall

2008·1h 51m·★ 7.1·Nicholas Stoller

Themes: vacation, hawaiiFans also likedComedy & Romance & Drama

The Idea of You

2024·1h 56m·★ 6.3·Michael Showalter

Themes: cougar relationship, older woman younger man relationshipComedy & Romance & Drama

Same Time, Next Christmas

2019·1h 30m·★ 6.1·Stephen Herek

Themes: hawaii, holidayFans also liked

From Here to Eternity

1953·1h 58m·★ 7.6·Fred Zinnemann

TMDB recommendsRomance & Drama

Couples Counseling

2016·1h 28m·★ 5.6·Alexandre Reinecke

TMDB recommendsComedy & Romance

The Santa Clause

1994·1h 37m·★ 6.6·John Pasquin

TMDB recommendsDrama & Comedy

Sister of the Bride

2019·2h·★ 6.1·Sam Irvin

TMDB recommendsRomance & Comedy

Dead Again

1991·1h 47m·★ 6.8·Kenneth Branagh

TMDB recommendsDrama & Romance

Stuck in Love

2013·1h 37m·★ 7.2·Josh Boone

Fans also likedDrama & Comedy & Romance

People We Meet on Vacation

2026·1h 56m·★ 6.6·Brett Haley

Fans also likedComedy & Romance & Drama

Summer of '42

1971·1h 43m·★ 7.2·Robert Mulligan

Fans also likedComedy & Drama & Romance

Enough Said

2013·1h 33m·★ 7.0·Nicole Holofcener

Fans also likedComedy & Drama & Romance

Something's Gotta Give

2003·2h 8m·★ 6.8·Nancy Meyers

Fans also likedDrama & Comedy & Romance

Venus

2006·1h 35m·★ 7.1·Roger Michell

Fans also likedComedy & Drama & Romance

The Four Seasons

1981·1h 47m·★ 6.8·Alan Alda

Fans also likedComedy & Drama & Romance

Enemies, a Love Story

1989·1h 59m·★ 6.6·Paul Mazursky

Fans also likedComedy & Drama & Romance

How Good Is Flirting with Forty?

Ratings across IMDb, Rotten Tomatoes, Metacritic, and TMDB, plus our verdict.