Jack Goes Boating (or See You Next Summer, as an international title) is a romantic comedy that showcases Jack as a limo driver. He is endearing and a little bit socially maladjusted. He spends most of his time with his friend Clyde and his wife Lucy. Through them he met the fragile and clumsy girl Connie and falls in love with her. To seduce her, Jack learns to cook with tenacity, begins to dream of a new career and will even learn to swim. Jack insists on keeping the promise he made to Connie when they met: a boat ride in Central Park! But while Jack and Connie are trying to overcome their inhibitions without renouncing their ideals, Clyde and Lucy starts to crumble the couple...