Philip Seymour Hoffman stars in his directorial debut in Jack Goes Boating, a film that is adapted from his acclaimed Off Broadway play. Considering Philip Seymour Hoffman is one my favorite present-time actors, keeping my expectations for the film in-check was troublesome if not impossible. Still, I try to give an unbiased review of this indie film, which I confess was not easy.

Jack Goes Boating is about a single shy limousine driver in his 40s named Jack (Phillip Seymour Hoffman). His best friend happens to be his co-worker named Clyde (John Ortiz). Clyde’s wife Lucy (Daphne Rubin-Vega) works in a funeral home with Connie (Amy Ryan). Connie is also single and shy so Clyde and Lucy decide to play matchmaker as they both seem perfect for each other. They invite Jack and Connie over for a dinner date.

Going boating is somehow brought up in conversation and Jack, without realizing, makes the mistake of setting a date with Connie in summer, after they had just met. You can tell he is uncomfortable around women. Good thing for Jack is she is not fazed by the six month future date, but the bad thing for Jack is he does not know how to swim.

A similar mistake is made on their next encounter which takes place in a hospital. The two both agree that waiting for summer to come is going to be a while so Jack comes up with the idea of cooking her dinner. The suggestion makes Connie very happy and confesses that no one has ever cooked for her before. Jack realizes that he not only has a place to cook, living in the basement with his Uncle, but he does not even know how to cook. Jack continually puts himself these situations but seemingly not on purpose but rather out of sheer awkwardness Jack possess as a conversationalist.

Luckily for him, Clyde is there for him. Clyde bails Jack out by teaching him how to swim and letting him borrow his kitchen to cook in. And if that was not enough, Clyde even knows someone that can teach him how to cook. Needless to say, Clyde is a friend you can count on.

However, Jack gets the opportunity to return the favor to him when Clyde tells him that his wife has been cheating on him. Jack is no longer the one in need of help. Although, Jack admittedly states that he cannot relate to the situation, he still helps Clyde by allowing him to vent his problem.

As Clyde’s relationship with his wife is on a downward spiral, Jack’s is just starting to blossom. We see more than them just changing roles with their relationships, we see a transformation among their lives. The ending is up for interpretation but I think Clyde is ultimately the one looking up to Jack and perhaps be the one that dependents on him more now, instead of the other way around.

The scenes at times are almost painfully awkward but it fits because both Jack and Connie are awkward too. For an example, when Jack visits Connie when she is in the hospital, he brings his tape player and asks her to listen to a song. We are left to just watch her as she is listening to the music with headphones on and they say nothing. Realistic? Yes. But a little strange as a viewer, definitely.

The characters were not given much background at first, instead the film jumps right in and you learn about them along the way. Which was a little off-putting at first but as you learn more about the character you can then start to connect with each of them. Eventually, we can empathize with the characters about what they are going through.

Jack Goes Boating is based on the play by Bob Glaudini and three out of the four main characters were in that play, so playing the role for them should have felt comfortable. One would have thought Amy Adams would have been part of that play as she easily fits right in but she was the new addition. I would have liked to have seen her up for Best Supporting Female for the Independent Spirit Awards this year instead of Daphne Rubin-Vega who played Lucy.

Philip Seymour Hoffman is one of the most under-rated, or at least forgotten about, current actor on screen. His acting performances are nothing short of brilliant and here is no exception. He seems nature playing the shy and vulnerable character which is one we have seen from him on a few films.

The soundtrack on Jack Goes Boating was both pleasant and fitting. It contains a few indie and folk bands which include a song from DeVotchKa, Cat Power and Goldfrapp as well as multiple songs by Fleet Foxes.

I had higher hopes for Philip Seymour Hoffman’s directorial debut but unfortunately the outcome was slightly above average. The dialog seemed out of place in a few spots and my guess is some scenes in general just worked better on stage. The transition from stage to screen is not an easy task as this film proves.