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Jack Goes Boating: Learning To Swim

“Don’t worry, I’m a good swimmer.” “I knew you’d be good.” “I am for you.”

Jack Goes Boating, directed by and starring Phillip Seymour Hoffman, is a film about how small changes make all the difference. It is one of the most romantic films I’ve ever seen, up there with Punch Drunk Love and both versions of Sabrina. It makes me hopeful for the future. It makes me think that some day, soon, I will find someone who loves me as much as I love them. Written by Robert Glaudini, based on his play of the same name, Jack Goes Boating isn’t big or obvious or epic. It is a film focused on subtle changes in the human condition, and how those small changes can lead to life changing things.

Jack is a lonely man. His two best friends, Clyde (played by John Ortiz) and Lucy (played by Daphne Rubin-Vega), set him up on a date with Connie (played by the super talented and gorgeous Amy Ryan). Things start slow. Jack is an awkward date, something I relate to. Things go pretty well in spite of this. Connie tells Jack that she would like to go boating when the weather gets better. He can’t swim. So Clyde starts teaching him. I can’t swim, and while this might not seem like a big deal to some people, it reflects my inability to be a fully functioning adult. One of the last things my father did for me, before he died, was to start teaching me how to swim. I can say without hesitation that Jack Goes Boating was a major influence on me in this regard. I wanted to make myself better, hopefully for the day that I met a woman whom I could spend my life with. I didn’t fully learn how to swim, but I did conquer my fear of being underwater, which I can thank my father for, someone who was always there when I needed him.

Phillip Seymour Hoffman was, as you know, an actor of supreme talent. He takes to directing with the same subtle, but powerful, approach that leaves plenty of room for the personalities and abilities of his actors. Amy Ryan is so damn beautiful here, and reminds me of a woman I know who I thought for a while was someone who would love me. She has the same gentle soul, and when I watch her in this movie, a deep sadness overcomes me. But joy too, mirrored off of what could have been, and the belief that someday I will find my way.

This is a four actor job, and the way the characters play off of each other is a pleasure to watch. The chaos and alternating hilarity and emotional desolation that comes in the scenes where Clyde just can’t let go of the betrayal of his wife with another man is powerful, desperately sad and so real. Jack learns how to swim and he learns how to cook. All of the preparation for his meal for Connie comes to nothing. “This always happens.” “What?” “Whenever there’s anything good, it fucks up.” “It fucked up, but it fucked up because *we* forgot.” “No, you fucked it up because you made a fucking toast! “Because I love you. We all love you. We forgot the food because you were being loved. That’s the important thing to remember.”

Clyde and Lucy remind me of two of my dear friends Conor and Sinead, who have supported me through endless crises and have always stood by me when I was at my worst. I am almost as upset by the ending of Lucy and Clyde’s relationship here as I would be if my two best friends were ever to split up. When you know that people love you for who you are, and also who you could be, you are fighting from a corner that can succeed even in the most dire of situations. I love them both with all my heart. When I show Jack Goes Boating to someone, I get nervous. What if they don’t like it? Sometimes art is a personal thing. To understand it, is to understand me. I see myself in Jack, and I hope that some day soon I can stand up and be a real, verifiable, adult man.

My favourite scene in the movie comes with the transcendent beauty of Bill Evans’ ‘Peace Piece’, while snow falls all around. If you haven’t heard ‘Peace Piece’, well, you’re really missing out. Have a listen here. I’ll wait…. See? This scene is just perfection. “I liked the movie. Thanks for taking me.” “It was intense.” “I like scary ones.” “It’s getting dark already.” “It seems like only two seconds we’ve been talking. Now we’re snow people.” “I like talking to you.” “I should invite you up, but my place is a mess. I’m gonna clean it and I’ll invite you up next time.” “Mine’s worse.” “I’m usually neat, well not neat, but not disgusting.” “I’m really glad you’re better.” “Almost. I’m getting there.” “Maybe a little goodnight kiss?” “Maybe.” “Nothing overwhelming.” “Okay.” “Night.” “Night.”

This is something that expresses with such purity what I have been searching for in my life for what seems like forever. Two bravura performances that get to the heart of why we endure such hardships in the search for love. It is soft and sweet and something that always moves me. Hoffman has had so many amazing performances through the years that it is easy to overlook Jack Goes Boating as a minor role, but this scene shows that it is among his very best, and in my opinion unsurpassed. For its beautiful heart, and the graceful way it depicts the struggle for love and acceptance and peace. I am reminded of the great Isley Brothers song ‘(At Your Best) You Are Love’. That song goes: “But at your best you are love, you’re a positive motivating force within my life. Should you ever feel the need to wonder why, let me know.” I can’t imagine a time when you would doubt what you mean to me, but if you do, let me know.

You believe in every word that Jack and Connie say to each other. You believe that these are two real people, trying to navigate their way through all of the bullshit that comes from being alive. Two people finding each other when they needed it most. Sure, it doesn’t have the sheer weight of a role like The Master, but it has so much subtlety and emotional maturity that it doesn’t matter. It is a terrible shame that Hoffman never got to direct another movie, as if Jack Goes Boating is anything to go by, he could have done great things.

Jack Goes Boating is the story of one relationship beginning and one that is ending. As Jack and Connie walk away together, leaving Clyde alone, we see ourselves, and the many loves that we experience in our lives. It is not the grand gestures that make a difference, but the small, human decisions that make a positive impact on those around us. This is not some grand, epic English Patient, star crossed lover situation. This is the story of real people, and the seemingly insignificant choices that we make, that can turn a fractured isolated person into a full human being.


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Written by Paul Casey

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