Jack Goes Boating (2010)

Jack is a shy and awkward man who drives a limo and lives an unassuming life. His friend and co-worker, Clyde, and his wife Lucy, feel sorry for Jack and set him up on a blind date with Connie. Connie shares Jack's shyness and awkwardness, but through each other they seem to be able to find solace within themselves. Trouble might be brewing in paradise though, as Clyde and Lucy's marriage stumbles just as Jack and Connie's relationship grows.