In "Return to the Cotton Club", Charles 'Diggs' Whelan comes to Fantasy Island to get a big break in his singing career. He sacrifices his chance to stardom by helping a young singer at "The Cotton Club". And in "No Friends Like Old", Doreen Murphy wants to impress her old college friends and win their respect, but soon learns that money can't buy respect.
In "Roller Derby Dolls" a manager of a sporting goods store wishes to own and manage a professional sports club. And in "Thanks A Million" A waitress from Arkansas along with an auto worker and an owner of a large appliance store arrive to compete in a contest.
Mr. Bracken wants Herman to escort his daughter Susan around, but takes a dim view of things when the two become romantically involved.
To save Crawford's butt, the gang has to pull an all-nighter to get him out of a jam. Herman and Heddy, Bracken and Crawford, and Louise and Jay end up pairing up and each learn something new about the other on an intimate personal level as they struggle to meet the deadline.
It's time for a near-end-of-scene flashback episode to save money, as Herman recalls his adventures in New York while deciding whether to stay where he is or go back to his hometown in Ohio to accept a new job.