Jack Goes Boating

Adapted from Bob Glaudini’s play of the same name, Philip Seymour Hoffman’s directorial debut, Jack Goes Boating, tells the simple tale of Jack (Hoffman), a shy, fortyish limo driver with a fondness for pot and reggae music — he likes it because it sounds happy — who meets Connie (Amy Ryan) for a blind date set up by Connie’s co-worker Lucy (Daphne Rubin-Vega), who is married to Jack’s best friend and fellow limo driver, Clyde (John Ortiz). As the young couple tentatively come together, breaking through layers and layers of awkwardness and low self-esteem, Clyde and Lucy’s marriage begins to dissolve because of Clyde’s inability to get over an incident from their past. All the while, Clyde gives Jack swimming lessons so that he can take Connie on her dream date — a boating trip on the lake., Jack is a shy limo driver just over forty in New York. His only hobbies are smoking weed and listening to reggae. A colleague unites him with Connie, who also doesn’t have the best self-confidence. Together they try to work their way through all the awkward silences and converge., In this poignant comedy-drama, quirky loners Jack (Philip Seymour Hoffman) and Connie are fixed up on a date by a married couple. As their new relationship begins to make their troubled lives better, Jack takes swim lessons in order to give Connie her dream date on a boat. Meanwhile, the couple who brought them together finds their marriage falling apart. Directed by Philip Seymour Hoffman.