Do the pictures in our minds play out in real life? Do our dreams open up new possibilities? Can the painful pictures of the past tear apart our future?

In Jack Goes Boating, there is an intriguing interplay of vision, possibilities, and reality. Jack is a limo driver who hopes to get a job with the MTA. Connie is a telemarketer for a grief support program marketed to mortuaries. Clyde works with Jack and is married to Lucy who supervises Connie at work. When Clyde and Lucy set up Jack and Connie for dinner, the two hit it off despite their social awkwardness. Soon Jack is looking forward to taking Connie boating when summer comes. The problem is that Jack can't swim, so the thought of going out in a boat seems dangerous.

Fears and overcoming fears play prominently in the film. Clyde (a wonderful friend) begins teaching Jack to swim. Part of the instruction is teaching him to visualize what he wants to do. That skill is something that Jack begins making use of for all the things he wants to do. With each visualization he gains confidence as he moves towards goals that fill further his relationship with Connie.

Connie has her own imagination—often in the form of sexual fantasy—that seems to be an outgrowth of her fears but evolves into her desires for Jack. I found Connie the most interesting of the characters. She has a sense of fragility and longing. We aren't sure what pain there may be in her past. Maybe it is just a sense of rejection, but it seems like she is struggling more than the others with a fear of fully encountering life. For Connie, the pictures in her mind are sometimes something that protect her, but also prevent growth. At other times those visions give her an opportunity from freedom.

The pictures in Clyde's mind come from an affair that Lucy had several years earlier. He has been hurt and he is not able to let go of the pain or what he has imagined of that time. Those images are destructive to his own happiness and to the relationship between him and his wife. If not dealt with, those visions have the power to destroy him just as much as Jack's visions have the potential of liberation.

In the Sermon on the Mount Jesus said: "The eye is the lamp of the body. So if your eye is healthy, your whole body will be full of light; but if your eye is unhealthy, your whole body will be full of darkness. If then the light in you is darkness, how great is the darkness!" (Matthew 6:22f) This is not so much about our physical eyes as it is about allowing ourselves to see light or darkness. Jack is learning to see light, but Clyde only sees the darkness. Connie struggles between the two. Not everything goes according to their imaginations, but the ways they approach life through their visualizations are a large determinant in how they will survive the misfortunes that may come.

As a brief side note, the use of the Melodians song "Rivers of Babylon" is very interesting in the film. Jack is constantly listening to the song because he senses it has an inspirational power, even though he says he doesn't understand all the words. The reggae beat certainly is uplifting. The lyrics are adapted from Psalm 137, one of the most heartfelt laments in the Bible—the sorrow of the exiles being ridiculed by Babylonian captors. (There is also a bit of praise in the song from Psalm 19.) That interplay of sorrow and joy that the song represents is very apt for the ways joy and sorrow mix in the lives of these characters.