Jack Goes Boating is a well-made movie, starring and directed by the late Philip Seymour Hoffman. The acting is good, but the storyline is relatively uninspiring. At times, I couldn’t relate to the characters or why they said something or acted in a particular way.
The movie centers on four characters: two friends who drive limos in New York City, a girlfriend and the woman she works with at a mortuary. Jack seems to be floating through life until his friend and limo co-worker sets him up with Connie at the mortuary. They hit it off and Jack finds himself growing and stretching in order to do things for Connie.
In the midst of swimming lessons from his friend Clyde, Jack learns to visualize. First to visualize himself blowing bubbles underwater and then swimming laps. We see him stop during his walk about town to visualize swimming while moving his arms and head in the correct rhythm. He later applies this technique to preparing a meal for Connie…a meal that he somehow came to promise her he would cook for her—although he does not cook and his kitchen consists of a hot pot. He practices cooking the meal over and over, both literally and through visualization. Practice and visualization. Visualization and practice.
Jack and Connie seem new to relationships. Both are quirky with some hangups. As they progress in their interactions, Jack gets pulled into the drama that is Clyde’s and Lucy’s relationship. The curtain on what seemed like a stable relationship gets pulled back. Despite their insistence that most relationships go through infidelities and you just have to deal and get over it, clearly they aren’t dealing or getting over it. In the end, as Jack’s and Connie’s relationship blossoms, Clyde’s and Lucy’s ends.
The title is a nod to the first date that Jack and Connie discussed during winter when they met. A boat outing during summer. Alas, Jack doesn’t know how to swim, which leads him on his quest to learn. His quest which takes him out of his present situation for another person.