“My Last Five Girlfriends” takes that most reliable of genres, the romantic comedy, and elevates it to amazing heights of intelligence and creativity. For this particular story, love is not a state of mind but rather an analytical process, one that can be so confusing, complicated, and heartbreaking that it ultimately may not be worth the time and effort. Duncan (Brendan Patricks), a British structural engineer, is at a point where he’s desperate to know how love is supposed to work, his last five relationships having ended rather unpleasantly. What went wrong? If he had done something differently, would that have changed any of the outcomes? He narrates the film not as a reflection but more as a deconstruction, as if to say that, although he has already participated in the events, he’s no closer to understanding them, and in all likelihood never will be.
 
That doesn’t make this movie a tragedy, although it does imply, with great frustration, that no matter how many times one has loved and lost, there’s no insight one can apply to a new relationship after the previous relationship’s failure. Each of Duncan’s girlfriends is unique both in back story and personality, which may account for this problem. Then again, it’s quite possible that, for all the analyzing he does, Duncan is remarkably imperceptive. How else to explain his failure to find the right woman five times in a row?
 
Adapted from Alain de Botton’s novel “Essays in Love,” this movie is an astonishing achievement in tone and illustration, the ups and downs of Duncan’s love life cleverly displayed through a whimsical series of symbols, visual gags, imagined scenarios, and cinematic tricks that in any other film might have seemed obvious. As he flies home, for example, he meets girlfriend No. 1, Wendy (Kelly Adams), whose life story gets the visual treatment when the cabin magically morphs into a funhouse ride; she and Duncan glide past scenes where crudely dressed Barbie dolls stand in place of more lifelike animatronic figures. This is, we quickly discover, a preview of coming attractions, Duncan eventually wandering into an imaginary carnival where rides represent his subsequent relationships. One of these is a rather twisted-looking roller coaster, the track navigated not by a traditional train, but by a line of red high-heeled shoes.

Other flights of fancy weave in and out of the story, the funniest being a conversation between Duncan and his newest girlfriend’s plush elephant, brought to life via puppetry. We also see an advertisement similar to a Match.com testimonial, camped up by religious imagery and a nostalgic 1950s graininess. Writer/director Julian Kemp handles this not merely as a gaudy display of imagination, but as a thoughtful examination of the madhouse that relationships can be – sometimes they’re a lot of fun, but they can also be quite taxing, especially when it seems no one knows what they’re looking for. Many go into a relationship thinking they know exactly what they want, only to realize that the people they envision are usually never the people they actually are.
 
Duncan’s first four relationships are fairly inconsequential, despite giving Duncan quite a bit to think about. It’s the fifth relationship with Gemma (Naomie Harris) that we’re meant to focus on, not only because it’s the longest lasting one of the story, but also because it’s the most compelling in exemplifying Duncan’s complicated situation. Gemma is a sweet girl – attractive, outgoing, intelligent – but as time goes on, Duncan begins to wonder if everything she says is really just a coded language. Eventually, he finds that she doesn’t do well with happy situations; she’s much better off with the idea of happy situations and the memories they bring. This relationship is symbolized by a carnival drop tower that lifts Duncan to stratospheric heights and has no visible top. Imagine what would happen if the car were to fall.
 
I’ve seen a lot of romantic comedies, and I’ve generally been harsh on them. They’re either formulaic, unrealistic, about characters that have no truth to them, or as in most cases, all of the above. The greatness of “My Last Five Girlfriends” is not only that it’s a triumph of imagination and style, but also that it tells a charming story with engaging characters. The otherworldly imagery works with the story, not in spite of it – it’s a vision of pure fantasy, and yet it’s never so outrageous that we fail to notice the emotions or the themes, both of which are grounded firmly in reality. I think the future of romantic comedies depends more on movies like this and less on movies like “My Life in Ruins,” “27 Dresses,” “Leap Year,” and “The Back-Up Plan,” all fantasies in the worst possible sense.

- Chris Pandolfi

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