
My Last Five Girlfriends
Directed by Julian Kemp
Produced by Tribeca Film Institute, Willing + Pilowsky Productions
A cerebral, melancholic examination of romantic failure and depression told through fragmented memories and fourth-wall-breaking analysis, grounded in philosophical inquiry rather than plot momentum.
Depressed and suicidal, thirtysomething bachelor Duncan – determined to find the secret to a healthy, strong relationship, – flashes back to his last five relationships (in the last four years) and considers what caused each one to fail. Based on the novel 'Essays in Love' by Alain de Botton.
Clusters
Questions people ask
Is My Last Five Girlfriends sad? Yes, very. More sad than 96% of films.
Is My Last Five Girlfriends violent? Barely. Less violent than 76% of films.
Is My Last Five Girlfriends scary? Not especially. Less frightening than 65% of films.
Does My Last Five Girlfriends end with hope? Not especially. Less hopeful than 64% of films.
Is My Last Five Girlfriends easy watching? About average. Almost exactly mid-range.
These describe how the film comes across, measured across the whole film and compared with other well-known films. They are not a content list — nothing here was counted or checked scene by scene, so for age-suitability or specific content use a classification board or a dedicated content-warning service.
Cinnamon Score
How much this film gives you that nothing else will, and whether it delivers.
Conventional, and it does not land.
How unlike any other film this one feels
How much more it delivers than it promises
How much audiences actually like it
Ensemble








Like My Last Five Girlfriends
Nearest across the full emotional profile.
Same Mood as My Last Five Girlfriends
Nearest on what's most distinctive about this one.
Like My Last Five Girlfriends, But Darker
Similar, pushed toward heavier and more intense.
Like My Last Five Girlfriends, But Lighter
Similar, pushed toward warmer and easier.
Like My Last Five Girlfriends, But Less Popular
Same territory, far fewer people have seen it.

















































