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"Jack Goes Boating" is a relationship drama. A tale about life, love, romance, marriage, dating and life again. It's about Jack (Philip Seymour Hoffman) a very awkward man whose married friends Clyde and Lucy set him up with Connie (Amy Ryan), a very awkward woman. Connie mentions that she would like to go boating, when the weather warms up. Jack would like that.

The rest of the film is about Jack trying to show Connie that he likes her and hoping that she likes him. Their awkwardness is heartbreaking and real and really sets the stage for watching love grow and eventually going boating. Hoffman and Ryan have a great connection; a very refreshing couple.

The film brings slowness to a whole new level, until things come to a boil. Some scenes really show the theatre roots of this film, and I always love those. There have been a lot of recent well done films based on plays and "Jack Goes Boating" is up there with the best.

There are some very subtle and interesting remarks about what makes a relationship work. It was uplifting but in a very awkward way, but also refreshingly real and ultimately cute. "Jack Goes Boating" is very slow, and adult and raw, but I recommend it.

'JACK GOES BOATING': Three and a Half Stars (Out of Five)

Philip Seymour Hoffman makes his directorial debut directing this film adaptation of the 2007 New York play he starred in. He and two of the three other lead stage actors (John Ortiz and Daphne Rubin-Vega) have returned to reprise their roles in the film, with actress Amy Ryan filling out the ensemble cast (replacing Beth Cole). Hoffman replaces Peter Dubois as director and makes a very impressive film making splash. Actor Robert Glaudini wrote the screenplay, adapting his play.

Hoffman plays Jack, a socially awkward but very sweet limo driver who's never had much if any experience with women or been in a relationship. Ortiz plays his co-worker and best friend Clyde and Rubin-Vega plays Clyde's long time girlfriend Lucy. The two set Jack up on a blind date with Lucy's new co-worker Connie (Ryan), a quirky and offbeat character that immediately takes a liking to Jack. It turns out as we soon find out that Clyde and Lucy have been having serious relationship problems for some time and take it upon themselves to devote a great deal of time to helping their best friend Jack with his new found love instead of working on their own.

The film is very slow paced, and seems aimless at times, and the story is almost non existent. It is a great character study though and the acting is all outstanding. Hoffman is of course amazing and Ryan is equally as wonderful. Ortiz and Rubin-Vega are more than adequate as well. The movie is obviously an actor's movie, being that it comes from a play that seems obvious, but Hoffman's directing adds a very powerful and unique touch as well. I really liked his character too and found him pretty relatable. The film shows a very strong and striking resemblance to one of my all time favorite films 'PUNCH DRUNK LOVE' (which Hoffman also co-starred in) but it's not nearly as well thought out and effective. Despite it's flaws it's still a memorable and unique film and worth the watch.

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Greetings again from the darkness. We all recognize the genius of Philip Seymour Hoffman the actor. This gives us one more example of his immense talent, but also puts his eye as a first time director on display. Not surprisingly, he comes through extremely well.

Based on the play by Bob Glaudini, three of the four main characters reprise their role from the stage production. Mr. Hoffman as Jack, John Ortiz as Clyde and Daphne Rubin-Vega as Clyde's wife, Lucy. The newcomer is the fantastic Amy Ryan ("The Office")as Connie. Jack and Clyde work together as limo drivers. Lucy and Connie work together for some odd funeral home specialist who markets some type of unexplained program.

All that really matters is that Clyde and Lucy arrange to have Connie and Jack meet. The apparent reason is that neither of them have any friends or social skills. What we then learn is that all four of these people are fractured. Scene after scene shows off the power of friendship and/or the faulty side of on-the-job relationship therapy borough about by cheating and secrets.

For the most part, the film has the feel of a stage production and moves very slowly as these type of people would. There are moments where individual weakness gives way to outbursts of emotions - and not all in a positive way. What is clear is that they each want the best for each other, but have no real feel for what's best for themselves.

I thought the film made some excellent points, but I was a bit disappointed in the hookah scene. That was the only scene that went too far and my guess is it worked better on stage. On the bright side, there are some tender, poignant moments and the acting is truly superb throughout the film. It is obvious that these four actors care very much for the story and these characters.

Perhaps the best way to watch Seymour's movie is without knowing a word about it as I did, and being enchanted by the magic on this film filled with the lights and shadows that can be found in two love parallel stories. Four characters played deeply by all the actors/actresses that carry you to the cold and meaningless streets of any big city where any story can develop to show you that we are still human and in any corner you have feelings and emotions. Beautiful screenplay where you follow the characters growing,applying the quote that the only normal people are the ones you do not know very well (Frédérick Jézégou). Perhaps being mature when you start a relationship means you can see around to other's mistakes trying to avoid them. Although not quite sure if you will finally behave in the same way. Brilliant film worth to see and being surprised by big Philip Seymour who should have a whole shelf in his house filled with Oscars.

This film is a tale of two couples in New York, whose love and betrayal unfold as their friendship progresses.

As a drama about the relationship between four people, you would expect the characters to be interesting, dynamic and simply alive. However, in "Jack Goes Boating", the characters are not sculpted or portrayed in the way that makes you care about them. None of them are interesting or sympathetic. There is little chemistry between the characters, seeing them in one room together is more like them having separate monologues about different topics. There is simply no connection between the characters, also between characters and viewers. The dialogs are bland and boring. The pacing is so slow that almost nothing happens in the 85 minutes of screen time. "Jack Goes Boating" to me is an abysmal failure.