Jack Goes Boating is a tale of love, betrayal, and friendship set against the backdrop of working-class New York City life. Jack and Connie are two single people who on their own might continue to recede into the anonymous background of the city, but in each other begin to find the courage and desire to pursue their budding relationship. In contrast, the couple who brought them together, Clyde and Lucy, are confronting the unresolved issues in their rocky marriage.