Seymour Hoffmann apparently died of drugs, so it's hardly surprising to find them featuring in his directorial effort. I enjoyed watching him learning to swim at the local pool, since I am pretty aquatic myself, but other than that the film lacked interest. Hoffmann's character's friend, Clyde, a fellow limo driver, confides to him that his wife had a two-year affair five years earlier and he still worries about it, even thinking she might be launching another. Hoffmann's character is horrified. Clyde introduces him to Connie, who works at Clyde's wife's office, selling mortician services and regularly getting molested by the mortician himself. They take a shine to each other. She lets him stroke her yoni, very gently, while conversing with him. Later in their relationship, she urges him to take her: "Overcome me", she says. He does so, and they seem idyllically happy. Meanwhile Clyde's relationship is on the rocks. Clyde hits cocaine and smokes hashish through a four-way hookah at Hoffmann's character's long-awaited dinner party for Connie. It's a disaster. They are obliged to escape. Later, they do go boating on the lake, so it ends happily ever after. Recommended.

This is an odd film. It starts off a lot like "Marty" and you feel a connection to the characters, but by the end, the film's more like "What Ever Happened to Virginia Wolfe?" (with all the arguing and substance abuse)...and that's a combination that just didn't sit well with me.Philip Seymour Hoffman had apparently starred in the play on which this film is based. In addition, he directed this low-budget project. How the two projects differ, I can't say, as I never had a chance to see the play.Hoffman plays a very shy and insecure middle-aged guy who is single. His friend sets him up with a lady who is equally shy and socially awkward. While neither really open up much at their initial meeting, over time a relationship slowly develops--at which time you learn more about the two characters. She is carrying some emotionally baggage and cold probably use a sex therapist, as she is phobic about being touched. He is incredibly unsure of himself and worries excessively about screwing up. In many ways, these two people did remind me of the characters in "Marty"--but they seemed to have MUCH more emotional baggage and were much more constricted emotionally. Because of this, the film was VERY dry and slow...glacially slow. Now I could have stood this, as I did connect with the pair. But, sadly, late in the film, the couple that introduced the two began to act almost exactly like Richard Burton and Liz Taylor from "Who's Afraid of Virginia Wolfe?"--and it just didn't fit with what had already been established. I wanted to see these two sweet screwed up folks together--not watch the Bickersons drink, do drugs and argue in the most vicious manner. It truly made my skin crawl.Overall, I would not watch the film. The first portion is great--the last, too dominated by the screwed up couple, was tough going. I think a tighter focus would have helped this film considerably. It's a shame, as the acting and some of the characters were nice.By the way, if you are interested, the title is referring to the risks Jack (Hoffman) is willing to take to change and grow. Despite a fear of water and unable to swim, he promises to take his new girl boating--and subsequently learns to swim and overcome his fear.

Seymour-Hoffman's directorial debut is a well-rounded little film about being positive no matter the circumstances; the possibility of a solution at the end of the tunnel and the value of perseverance.Jack Goes Boating relates the tale of four people whose stories are wound together. The premise is simple: one couple throwing a blind date for the other two parties. From this seemingly basic starting point, the characters undergo transformations, all of which are sprinkled with life-lessons and positive philosophy, all the more poignant for its stark backdrop of lower-middle class life. In this sense, there is a feel of La Vita è Bella about it, although admittedly Jack Goes Boating is not quite in the same league as the former.Phillip Seymour-Hoffman pulls off some typically sensational acting, as does Amy Ryan, with a complicated emotional role which she executes very well indeed.All in all, a high-class film, totally worth watching, but not something that leaves you with the feeling it ought to have won Best Picture.(Please take the time to say whether you found this review useful. Thanks.)

The late Phillip Seymour Hoffman's directorial debut of 'Jack Goes Boating' was not one of the better films he was associated with. Perhaps it was his stellar reputation that influenced viewers to heap accolades upon it.Hoffman chose to take on this project because he played the same role in the source material, an off-Broadway play (of the same title) produced in 2007. Also along for the ride were John Ortiz (Clyde) and Daphne Rubin-Vega (Lucy), who appeared in the original production.'Jack Goes Boating' is the tale of a socially inept limousine driver who works for his uncle and lives alone. He's one of those trite characters with a heart of gold, reminiscent of 'Marty', the 1955 Academy Award winner for best picture about a lonely Bronx butcher. Like 'Marty', Jack is self-effacing and sexually inexperienced; he meets up with Connie who is the equivalent of the wallflower Clara, an introverted woman who Marty ends up falling for.Jack is introduced to Connie by his best friend, Clyde, who also works as a limousine driver for Jack's uncle. It turns out that Jack's beau, Lucy, works with Connie at a funeral home where the mortuary director has his employees operate a side business selling seminars through telemarketing. Connie is also a dead fish like Jack and I suppose that's why they like each other. The story takes an unpleasant turn when Connie is sexually assaulted on the subway (must have been a few stops later, since we see the perpetrator eying Connie on a CROWDED train). Of course simple but sensitive Jack has the right touch and will ultimately help Connie get over her fear of sexual intimacy.As for Jack, he's busy filling out an application for the MTA (when jobs were still available!) and learning how to swim under the tutelage of Clyde since Connie wants to go boating. Another one of Jack's limitations (that he's really bothered by) is the fact that he doesn't know how to cook. So a chef friend of Lucy tutors him on how to prepare a nice casserole. Sure enough, the dark moment of Act 2 is when the four principals end up getting high and Jack's casserole goes up in flames. He locks himself in the bathroom and Connie has to coax him out. Meanwhile Lucy and Clyde have their meltdown when Clyde, in an act of retribution, invites Lucy's old flame she had an affair with, over to dinner.Very few people like Jack and Connie exist in real life. If they do, they certainly don't make for good drama. Instead of writing about people who like themselves (those who happen to have egos), the film's scenarist ask us to root for a couple of caricatures, plagued with substantial inferiority complexes. Of course there are always suckers who will be taken in by such sentimental, manipulative drama.While I admired Hoffman in 'Capote' and 'The Savages', I think his decision to choose this type of material for his directorial debut, was a mistake. It's unfortunate that he'll never get more chances to show us his talents as a director as he had already proved that he was a great actor.