​Jack & Connie

The film you're likely looking for is Jack Goes Boating, a 2010 romantic drama starring and directed by Philip Seymour Hoffman, which is also sometimes known by the title Jack & Connie. The story follows Jack, a shy limo driver, as he tries to impress his girlfriend Connie by learning to swim and going boating, leading to a romantic drama about relationships and self-discovery.
Philip Seymour Hoffman got his big break with "Boogie Nights" and has since had huge successes with films like "The Talented Mr Ripley", "Magnolia" and "Mission: Impossible III". In 2005 he won an Oscar for his work in "Capote". "Jack Goes Boating" Philip Seymour Hoffman's directorial debut is a romantic feel-good comedy from the producers of "Little Miss Sunshine" and "Away We Go".

Jack is a shy limo driver in his early 40s in New York. His only hobbies are smoking weed and listening to reggae. His hobbies are, in short, smoking pot and listening to reggae because the music is so happy. A colleague sets him up with Connie, who also doesn't have the best self-confidence in the world. Together they try to work through all the awkward silences and get closer to each other.