My Last Five Girlfriends

My Last Five Girlfriends is a 2009 British romantic black comedy film directed by Julian Kemp starring Brendan Patricks, based on pop-philosopher Alain De Botton's book, Essays In Love (U.S. title On Love).^[1]

My Last Five Girlfriends
Directed by	Julian Kemp
Written by	Julian Kemp
Based on	Essays In Love (U.S. title On Love) by Alain de Botton
Produced by	Marion Pilowsky David Willing Michael Kelk
Starring	Brendan Patricks Naomie Harris Kelly Adams Cécile Cassel Jane March Edith Bukovics
Music by	Andy Blythe and Marten Joustra
Production company	Willing Pilowsky Productions
Distributed by	Paramount Pictures
Release dates	23 April 2009 (2009-04-23) (Tribeca Film Festival) March 2010 (2010-03)
Running time	90 minutes
Country	United Kingdom
Language	English

Plot

After yet another failed relationship, 30-something Duncan (Brendan Patricks) finds himself emotionally devastated and decides to embark on an unconventional journey of self-discovery. Determined to understand his pattern of romantic failures, he resolves to quiz his last five girlfriends to find out what went wrong in each relationship and identify his personal shortcomings in order to figure out how to find lasting love.

Duncan's quest takes him through a series of encounters with his former partners, each revealing different aspects of his character and approach to relationships. As he delves deeper into his romantic history, he seeks advice from increasingly bizarre and unexpected sources, ranging from self-help gurus to eccentric friends, while experiencing intense flights of fancy and surreal moments of introspection.

Through this process of painful self-examination and often uncomfortable conversations with his exes, Duncan begins to uncover the recurring themes and mistakes that have sabotaged his relationships. He starts to understand that his approach to love has been fundamentally flawed, treating romance as something that should come naturally rather than recognizing the effort and compromise required.

Finally, through his journey of discovery, Duncan comes to the profound realization that love is not the idealized fairy tale he had imagined, but rather a complex battleground of emotions, expectations, and personal growth where only those willing to fight for it—and adapt themselves in the process—can truly survive and find happiness.

Cast

• Brendan Patricks as Duncan
• Naomie Harris as Gemma
• Kelly Adams as Wendy
• Cécile Cassel as Rhona
• Jane March as Olive
• Edith Bukovics as Natalie
• Michael Sheen as Burnam
• Mark Benton as Alan
• Daniel Hoffmann-Gill as Will
• Sarah Rodriguez as Paula

Reception

Review aggregation website Rotten Tomatoes gives it a score of 32% based on reviews from 19 critics.^[2]