When the current members meet Jack, who builds low-income housing in more upscale neighborhoods, his application to join is rejected. The rejection stems from his oafish personality and an earlier confrontation with Bushwood President (and Miffy's father) Chandler Young's (Robert Stack) wife. The glamorous Cynthia Young (Dina Merrill) had tried unsuccessfully to persuade Jack to build his housing complex away from her neighborhood, but her less-than-subtle snobbery leads Jack to chase Cynthia with a bulldozer. It's actions like these that build a divide between Jack and Kate.