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In Philip Seymour Hoffman’s directorial debut, it takes motivation, a plan, and the help of a friend to break you out of your rut.

Jack's not a picture of style in his wool cap
Jack’s not a picture of style in his wool cap

Learning to Swim

Jack (Hoffman) and Clyde (John Ortiz) drive limousines for a living. They aren’t particularly smart or handsome or rich. They’re just guys. Jack is a little more socially inept than Clyde, who is married to Lucy (Daphne Rubin-Vega).

Jack is single, and Clyde thinks it’s about time Jack had a girlfriend. He sets him up with Connie (Amy Ryan of The Wire), a coworker of Lucy’s who is almost as socially inept as Jack. Jack and Connie grow closer in their awkward way. Connie seems to be afraid of men, which slows their courtship down to a pruder pace.

Over the course of a few dates, Jack decides to do a few things for Connie. An offhand remark about boating sends Jack to the swimming pool with Clyde to learn how to swim so that, come spring, he can take Connie on a boat. An offhand remark about “dinner someday” turns into Jack’s inadvertent promise to cook Connie a meal in a month. Jack gets cooking lessons from a man who had an affair with Lucy — it’s okay, Clyde knows about it — which it adds a pinch of tension to Jack’s slow increase in skills and self-esteem. It also reopens Clyde and Lucy’s old wounds and sends them on a gradual descent counterweighing Jack’s rise.

Very good casting and acting help the movie immensely. Hoffman is a boy in a man’s body. He is not so low-functioning as to have a condition, he’s just a little slow and thick. His friend Clyde does much better, without necessarily belonging to a higher caste. Clyde looks sharp in his suit, tie, crisp white shirt, and groomed salt-and-pepper moustache and hair. Only his boyish personality belies his uniform. Hoffman, in contrast, covers his suit with a puffy canvas jacket and hides his blond dreadlocks with a brown wool cap. They live somewhere in-between Precious and Wall Street: Money Never Sleeps (and much closer to Precious).

Understanding the Drama

Jack Goes Boating is competently directed. The directorial duty that Hoffman handles best is working with actors. He coaxes good performances from everyone and never sacrifices character for the demands of the plot. For example, Connie’s coolness toward sex causes some tension. A moment of interruptus tries Jack’s patience and Connie’s ambivalence. The characters react with characteristic emotion but it’s not an explosive scene or an excuse to send the plot off in another direction. It’s a scene that exposes the characters’ raw nerves and shows us who they really are — Jack with his good heart and humble self-image, and Connie with her sympathetic and ambivalent mein.

A fellow critic said Jack Goes Boating was obviously a filmed play but I didn’t find the movie too claustrophobic. The visual flourishes — jack visualizing his lessons to help him learn — didn’t seem gratuitous to me until my friend pointed it out, and even then I didn’t think it was overly flashy, just another way to get inside Jack’s head.

I would concede that the final climactic conflict was predictable, but I also thought that it was just one scene out of many, and not the keystone for the whole film. It didn’t ruin what had gone before.

If I had any doubts about the competence of Hoffman as a director the final two shots put them to rest. They subtly change the focus and hint at the next stage of the story. They really show that Hoffman understands the drama, pinching our story closed rather than leaving it open like an easy “happily ever after.”

Jack Goes Boating is not earth-shattering; the film’s slow but steady pace may turn off mainstream crowds, but seekers of drama will like Jack Goes Boating. With likeable rooting interests all around and a good story arc Jack Goes Boating is a decent fall drama.