Hope lures former teen star Connie Carlucci, who was Hope and Gloria's childhood idol, from seclusion to co-host Dennis' show, despite his disgruntled aversion to sharing the attention. But it quickly become apparent that in contrast to the perky, positive character she played, Connie is now an embittered drunk.
Gloria suffers a crisis of nerve after she finds a note she wrote to her future self 15 years ago setting out her life's goals, all of which remain unaccomplished. To regain her equilibrium she sets out to carry through on at least two: learning to scuba dive (with a reluctant Hope in tow), and erasing a graffito about her former teacher from atop a water tank.
When Gloria nervously accepts a date with her handsome professor, she turns to Hope for a quick course in culture and ladylike comportment. The makeover inspires Hope to pick Pygmalion for her theater group, and she, Dennis and Louis perform in an outlandish production, attended by Gloria and her urbane escort.
Hope and Gwillem hustle to produce the momentous 5,000th telecast of The Dennis Dupree Show, and wind up with an eye-popping pastiche, featuring clips of Dennis with the likes of Wiliam Devane and Grant Show, a trip down Memory Lane with Dennis' first piano teacher, Miss Mae, and a special appearance by the Alelgheny Women's Triple Trio. Hope lines up 500 celebrities, only to have her plans doused by a torrential rainstorm that shuts down the airport. Dr. Joyce Brothers shows up but refuses to stay and save the day. Meanwhile, Gloria hits the books with fervor as a new night school student, but six-year-old Sonny is mad at his mommy for not being home and lashes out at babysitter Hope.