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Phillip Seymour Hoffman has truly evolved into one of our premium character actors. From his Oscar-winning portrayal of Truman Capote to his role as the lingering Father Flynn in “Doubt,” Hoffman has proven time and time again that he is a complete performer. He never plays the same part twice and always brings new zest to every one of his characters.

After nearly twenty years of screen acting, Hoffman finally makes his directorial debut in “Jack Goes Boating,” a well-shot and strongly acted first feature. The weak link of “Jack Goes Boating” is its narrative, which never strikes the right tone.

In what I guess is supposed to be a dark romantic dramedy, Hoffman casts himself in the title role in addition to directing. Jack is a middle-aged, socially awkward limo driver who wears a winter cap almost all the time. His only friends are a fellow limo driver named Clyde, played by John Ortiz, and Clyde’s wife Lucy, played by Daphne Rubin-Vega.

“Jack Goes Boating” is based on a play by Bob Glaudini, which also starred Hoffman, Oritiz, and Rubin-Vega during its initial run. These are all talented actors who have clearly mastered their parts. Their characters are so ill at ease and confused though that after a while you start to get annoyed with them.

As Jack has never been in a long-term relationship, his pals decide to set him up with a friend from Lucy’s work. Jack’s blind date is a woman named Connie, played by Amy Ryan. Connie is sexually repressed and timid with low standards, making her the seemingly ideal mate for Jack.

As good as Hoffman is here, his character is fairly underdeveloped. Constantly wearing a winter hat and a pair of headphones, Jack comes off more mentally challenged than merely socially awkward.

Amy Ryan is a wonderful actress just on the brink of stardom with her Oscar-nominated work in “Gone Baby Gone” and reoccurring performance on “The Office.” In “Jack Goes Boating” she brings as much grace and charm to the role of Connie as any actress can.

But Connie is such a clumsily written woman who rambles on about the death of her father throughout her first date with Jack. She’s a bit like the Debbie Downer character on “Saturday Night Live,” only instead of being uncomfortably humorous is just uncomfortable.

At times the film reminded me of “Eternal Sunshine of the Spotless Mind” and “Punch-Drunk Love,” both of which told tales of romantically inept men whose lives are enriched by the love of women. I believed and genuinely cared about the romance between the leads in those movies though.

Here I never felt for a minute that Jack and Connie were really falling in love. They seemed more like two immensely insecure people settling for one another. The movie also meanders with a subplot involving Clyde and Lucy’s deteriorating marriage.

“Jack Goes Boating” is a movie with good intentions and some fine acting. But for a film that confronts many issues regarding marriage and finding love, it never decides what it wants to say about relationships. As for Hoffman as a director, he has a stylish eye for filmmaking and I hope this isn’t his last directorial outing. Next time around I just hope he can find better source material.

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