My Last Five Girlfriends (2009)

We meet Londer Duncan as he decides to put an end to any future painful romantic experiences, which for him means he must end his life (that is the big leap here--why not celibacy? Well, he does answer that question at the end). Over the next hour or so, we learn how he has come to this point. He reveals the five causes leading to this tragic effect: his failed relationships. While, it might sound trite, My Last Five Girlfriends is a captivating whirlwind of a tale, with hints of surrealism and wry quirkiness. As we witness each relationship in Duncan’s life promisingly unfurl and then painfully diffuse, the film cleverly drifts in and out of surreal imagery. For starters, as a transition to his subsequent female endeavors, he wanders through a fantastical theme park called "Duncan World." While each initially entice with the promise of quick thrills and endorphin boosts, things begin to excel too quickly or soar too high, and the landing becomes a painful splattering on the concrete. His relationships do tend to crash land in this way rather than just petering out. The thing about this movie is that our hero really pretty much screws up most of these relationships, either in part or full on, and while he voices an understanding of what went wrong, his assessment is completely out of synch with what we the viewer sees--so as he hurdles into the next relationship, we see all the pitfalls long before he does. It is classic British romantic comedy--you can see why their reputation as rather bumbling lovers comes from, and you can laugh with them, rather than at them, in this light movie.