For the most part, the characters of Jack Goes Boating are passive to each other and to the events that happen to them. Our titular limo driver Jack (Philip Seymour Hoffman, who also directs) gets set up with mortuary secretary Connie (Amy Ryan) because his best friend Clyde (John Ortiz) is married to her co-worker Lucy. Jack’s first date with Connie happens in Clyde and Lucy’s shabby apartment, where she talks about being sexually harassed while her father’s in a coma. Her sexual misadventures are exposed to Jack just as she is aware of his inexperience. Jack misses a chance to get an application for a job at the MTA. This baby step towards a better job and life feels unambitious but nonetheless realistic. For some reason, after these short introductions out of the way, the first act of the film doesn’t feel neither like an introduction nor a build-up. It’s one awkward situation piled on top of another.
The final act of the film shows its off-Broadway roots, that everything else before it is just fluff, yet what we see is also an intense payoff. Clyde reveals secrets, which makes the other characters open up. Again, Jack uses Clyde and Lucy’s apartment, show off his newly acquired culinary skills, but instead people and things get smashed because of hashish. We see Jack’s compromises in becoming the perfect person and mate for Connie. Connie, in watching Clyde and Lucy’s relationship crumble, doesn’t have a eureka moment but does something with her life to survive and be sane, as if by common sense. Clyde realises his altruism goes hand in hand with being life support for other people instead of being a man of his own, which doesn’t seem like a consequence but simply a terrible fate for a man. Jack Goes Boating is not the most original tragedy, but its downward spiral is very effective.