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My Last Five Girlfriends Review: Creative, Artistic, And Unique

My Last Five Girlfriends Review: Creative, Artistic, And Unique


A clever adaptation of international bestseller On Love, by Alain de Botton, in which Duncan is a young man determined to find the secret to a healthy, strong relationship. Along the way, he mines his last five doomed romances for clues.


This film doesn’t have a very happy start to it. When we’re first introduced to our main character (Duncan), he is writing a suicide note to all his ex-girlfriends who have obviously crushed his heart.

On the journey back through Duncan’s past girlfriends, we start out with girlfriend #1 Wendy, who, we’re told, Duncan had a 1 in 6 chance of meeting that morning. She seems quirky, cute, and oddly a perfect match for Duncan – but as the weeks pass, Duncan learns he never really had a chance with Wendy as she was just going through a rough patch with her ex.

As Duncan exits the relationship, he’s dispersed into a odd and slightly creepy theme park which mirrors his life. Creatively, this works well for telling the stories of Duncan’s romantic ventures.

He has just exited the roller coaster of ‘The Life of Wendy’ and he finds himself next in front of ‘The House of Olive’ – Girlfriend #2. Right off the bat, we discover Olive is a bit indecisive and all over the place, and Duncan is a bit too eager to please. Adopting whatever style and personality he thinks would appeal most to Olive, Duncan soon finds that courtship at an end as well.

Rhona was girlfriend #3. She loved shoes, sex, was incredibly clumsy, and she brought exotic additions to Duncan’s life – which most guys would count themselves incredibly lucky to find. But this is the first relationship we see Duncan as an ass in. After telling Rhona her new shoes (which she was in love with) looked like pelicans, and not just biting his tongue – their relationship, or in the metaphorical realm of the film, the roller coaster, comes to a screeching halt.

Next we have the unstable ferris wheel that was the relationship with Natalie. Another girl that seems perfectly enjoyable, but Duncan just can’t settle down with. The spark just wasn’t there, but why exactly was that? It seems to the viewer that Duncan is never really happy unless he’s with someone who isn’t really with him – such as with Wendy.

Next comes Gemma, a friend of Natalie’s, who Ducan starts falling for while still with Natalie. But there’s a 6 month break between Natalie and Gemma. A period which is represented by a barren desert in the film – full of a moment of silence and even a little bit of weeping. But as soon as the new year breaks, so does the next stage of Duncan’s life – Gemma.

When Duncan sees Gemma entering a grocery store, he stops off and has a bit of a stalk – which concludes with him throwing some socks into her bag to make the alarm go off. His rather elaborate and witty plan includes him interceding in the conversation between her and the security guard and cleverly implanting a question about if she would need to steal those socks for a boyfriend. Nope, Gemma was single, and we find ourselves amused and impressed with Duncan’s tactics – yet still convinced he’s devoid of the ability to develop an emotional bond with another female.

Before debarking on the new ride that is Gemma, Duncan makes all these promises that it’s going to be different this time. He’s going to learn from all his past experiences. And as time passes, the viewer actually feels like this relationship is different. But something starts to seem off with Gemma, and Duncan starts looking for problems. Trying to save what’s left of the relationship, Duncan takes Gemma on what is seemingly the perfect holiday in Paris. However, tensions are high – and a new dark phase of the relationship is entered which the film entitles “romantic terrorism”. For those of that have experienced a not so pleasant phase of a relationship that happens to mirror this stage – we can oddly appreciate and sympathize with Duncan, who a few girlfriends ago we were convinced was a total ass.

After the final demise of Duncan’s relationship with Gemma, we’re brought back to the first scene. Duncan is hoping that his suicide will prove that love is a deadly serious matter. That he was a martyr for love.

And while you may think the film ends there – there’s more to it. And for that – you’ll just have to check it out on Tribeca Film Festival on Demand!

Overall the film has a creepy carnival feel to it – like a slightly less happy “Amelie” but still hopeful, creative, and artistic. What’s so welcomingly refreshing about the film is how each story is told. With comical dating commercials to Barbies, giant shoes to talking elephant stuff animals – its way of storytelling is unique and a playground for the imagination. It’s also interesting to see this story from a male perspective. So many of these types of movies come from the female perspective.

It’s worth checking out if you decide to take part in Tribeca Film Festival on Demand, which is a great way to take part in the festival if you can’t attend in person. For more information check out

Grade: B

Review By: Emma Loggins

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Emma Loggins Emma Loggins is the Editor in Chief of FanBolt. As an internationally recognized "Geek Girl", Emma updates daily on the latest entertainment news, her opinions on current happenings in the media, screening/filming opportunities, inside scoops and more.  She’s been writing on the world of geekdom and pop culture since 2002 and is also considered to be one of the top Atlanta bloggers and influencers!


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