It's nice to run into films where admittedly, what goes on in the title actually does occur in the film, but Jack Goes Boating is a little more complex than that. And while the film, cast and (to a degree) story are muted, this might be one of the better films that has spoken to me personally in recent memory because of that understated manner.

Robert Glaudini adapted his play for the screen and Philip Seymour Hoffman (The Invention of Lying) directs his first feature here while also playing the title role. Jack doesn't know many people in New York, his friends are Clyde (John Ortiz, Pride and Glory) and his girlfriend Lucy (Daphne Rubin-Vega, Rachel Getting Married), and his job is a limo driver, so he doesn't get a chance to personally interact. However, Clyde and Lucy introduce Jack to Connie (Amy Ryan, Gone Baby Gone), and Jack finds himself falling in love with her.

The interplay between Jack, Clyde and Lucy is good, and the humor that comes from some of their scenes is funny in a modest way. Upon further review, it's worth noting that not only did Hoffman, Ortiz and Rubin-Vega appear in the 2007 play, they are all members of New York's LAByrinth Theater Company, which Ortiz co-founded and Hoffman is Artistic Co-Director of. They are well aware of each other's nuances, and adding Ryan to the cinematic version of the play feels like a seamless transition. Each gets their own individual moments in the film and they are all solid. Not having been exposed to Rubin-Vega's work before, I was impressed with how much depth she managed to give her performance.

Hoffman's performance is good, but I think in this case, it's less about what he does with Jack and more about what Jack does in the film. Jack is a bit of a disheveled mess, without much opportunity to talk to people he tends to immerse himself in his own world and is childlike to a degree. But in becoming enamored with Connie, he wants to become the type of person that he thinks Connie would like, and it improves himself in the process. It's admirable, even sweet, and that's the main thing that comes across in the film. His thinking to lose himself in a task for her, to repeat it over and over again, is charming to watch, especially if you're not easy on the eyes like Hoffman is.

And with Jack's rise in his development, he (and we) also witness some small fractures in the relationship with Clyde and Lucy, culminating in a dinner that Jack cooks for them (and in particular Connie), when Clyde and Lucy have a fight shortly after Jack burns the dinner. Jack erupts in rage. After he sees Clyde and Lucy yell at one another, one can only wonder if his urge to win Connie's love increased more.

I'm not a cigar-chomping, red meat and Budweiser consuming man; however I dip my toes into each one of those pools, and I'd like to think I can speak for a good portion of us and talk about the challenges that we find when we meet somebody who can possibly be the one. I think there's someone for all of us, and even those who might be a little self-loathing or skeptical about life can be inspired to change or improve themselves, particularly if it means earning the love of someone they find appealing. It's in that way that Jack Goes Boating struck a chord with me, as a guy who lost weight and gave up smoking for someone he likes and wants to spend as much time as possible with.

Anchor Bay shows off Jack Goes Boating in an AVC encoded 1.85:1 high-definition widescreen presentation and it looks OK. This being Hoffman's initial directorial effort I'm not sure how much consideration was given to the look of the film (or any breathtaking shots), but most of the action occurs in the evenings, with blacks that are fairly consistent though a bit lacking when it comes to providing contrast. Flesh tones are reproduced accurately, though the overall image lacks detail both in the foreground and background. This is more a film for the material and performances, but I can't imagine a noticeable uptick in quality from the standard definition version.

The Dolby TrueHD 5.1 surround track isn't bad. The film is almost exclusively driven by dialogue, though in larger sound-based scenes (the snow hitting the windshield from the plow, the smoke alarm going off in Jack's apartment) the soundstage is clear and well-replicated. Dialogue sounds consistent through the center channel and requires little in the way of user adjustment, and there's even a hint of directional effects and low-end fidelity here and there. It's not going to be confused for any demo quality discs, but it sounds fine on Blu-ray.

It would have been nice to at least get a commentary from Hoffman to recall his work on the firm, but in lieu of that we get two deleted scenes (1:52), one of which includes the best line I've heard a woman use to dismiss a flirtatious guy. Next is "Jack's New York" (3:51), which shares the cast and crew's thoughts on shooting in New York and how it was approached from a production design aspect of things. "From the Stage to the Screen" (4:35) examines the work put into adapting the play for film, while the trailer (2:22) completes the disc.

Jack Goes Boating is a dark, quirky but ultimately charming story about falling in love and the lengths you might go to win the love of the person you admire. The performances are solid if not better than usual and it's got its fair share of laughs to boot, and definitely worth checking out for a change of pace.