“Jack Goes Boating†is along the lines of what one would expect from Phillip Seymour Hoffman’s directorial debut – a thoughtful little indie that explores something complex, or at least scratches the surface. While the film makes an attempt at some heavy subject matter, it does so with little depth, making it hard to care about most of the characters and the film in general. That’s not to say that the film doesn’t have some good qualities. It draws an interesting parallel between two very different sorts of love – one is delicate and innocent, the other is strained and nearly broken.
Hoffman’s character, Jack, is a lonely guy whose life consists of driving a limo and hanging out with his best friend and fellow driver, Clyde (John Ortiz) and his wife Lucy (Daphne Ruben-Vega). Sensing his internal misery, the couple decides to set Jack up with Lucy’s friend Connie (Amy Ryan) – a kooky funeral home employee with a penchant for negativity. Upon first meeting, both Jack and Connie make equally awkward first impressions, with Jack dressed in a suit, tie, and an unnecessary wool cap, and Connie telling the morbid tale of watching her father gasp for his last breath. Despite all this, some form of a relationship begins to take shape. But before he can be the man Connie needs, Jack must shake himself out of his depressing frame of mind and take some lessons in self-improvement from Clyde.
But while Jack and Connie are carefully learning to love one another, Clyde and Lucy are struggling to keep it together. Since he has never been in love before, Jack is unable to understand the problems Clyde and Lucy are having. Clyde, easily the movie’s most interesting character, knows deep down that his relationship with Lucy is failing, which could be the reason he so desperately wants to see things work out between Jack and Connie. In some way, Clyde seems envious of the innocence concerning the couple’s budding romance as he seeks to put the complexity of his own relationship out of his mind.
The main problem with “Jack Goes Boating†is that it focuses on two characters (Jack and Connie) that are neither likeable nor believable. The naïveté and forced quirkiness of these two characters is a little bothersome at certain points, especially when you consider that these are not exactly kids we’re watching, but middle aged people. The far more interesting storyline is the one between Clyde and Lucy. These two characters are what make this film worthwhile as we watch Clyde attempt to deal with and move past his wife’s indiscretions. The other issue this film suffers from is its limited plot. Besides the parallel love stories, the movie has little going for it. This may have been compensated for if Hoffman and Ryan’s characters were able to offer us a little more. Instead we are left with a simple but decent plot – one love grows and flourishes while the other crumbles and fades into nothingness.
But the cutesiness of Jack and Connie does not distract too much from the film’s stronger elements, and what the film does offer us is a look into the lives of four desperately insecure people, and the movie does a good job of communicating that. They are a little older than they would like to admit and they each fear spending a life alone. Despite all its weak points, “Jack Goes Boating†leaves you with something to think about; will Jack and Connie face the same fate as Clyde and Lucy? Will their love remain innocent and blissful? Given that he has never been in love, how will Jack handle the complexities of a relationship?
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