I struggled getting into Jack Goes Boating early. The attempts at witty dialogue mostly fall flat, and my initial reaction was that despite the star power of Philip Seymour Hoffman as director and lead actor, this is a surprisingly ordinary, mediocre indie dramedy that looks and sounds like dozens of other indie dramedies I’ve seen in my life.
Gradually, though, it won me over. Not in a huge way certainly, but as it got more serious, I felt myself becoming more interested in the story and caring about the characters to at least some degree.
There are four main characters in the movie—a couple who have been together long term, a single male friend of theirs (Hoffman), and a woman with whom they have fixed the friend up. The film is about this new couple and whether things will work out and they’ll develop a relationship, and the long term couple and the serious flaws in their relationship.
The Hoffman character is lonely and is really giving it his best effort to impress his potential new girlfriend and get something going with her. She’s not a complete basket case, but she’s probably somewhat more messed up than he is. Arguably neither one’s all that great a catch, especially her, but they may well be good for each other.
On the one hand, the fact that the other couple has managed to sustain a long term relationship puts them in a position to mentor the new couple. But on the other hand, the more the Hoffman character finds out about their bickering and infidelity and hurtful behavior, the more he realizes they’re a negative example rather than something to emulate, and the more scared he becomes that a good relationship is just too hard to pull off.
The acting is solid throughout in Jack Goes Boating, and other than the fact that the attempted humor ranges from average to somewhat below, the dialogue is generally fine. I found the film to be thought-provoking enough about relationships and friendships and flawed people trying to help each other to just barely tip it into the thumbs up category. Not a must-see, nothing that hit me on a real deep level, but an interesting and intelligent enough film to have some value.