Jack Goes Boating (2010)

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 swim lessons so that he can take Connie on her dream date - a boating trip on the lake.