Mrs. Howell decides to engineer a romance between Gilligan and Mary Ann.

After Gilligan saves Mrs. Howell's life, Mr. Howell decides to make him his son. He immediately puts Gilligan through basic training to be a millionaire's socialite son (dream sequence), changing the way he walks, talks and dresses. However, Gilligan and the rest of the castaways miss the "old Gilligan."

Gilligan suggests a beauty contest to decide which of the three women will become "Ms. Castaway." Mr. Howell attempts to sabotage the other contestants by spreading glue on the stage before Mary Ann's big dance scene, and by shooting spit-wads at Ginger while she performs. The Professor blows pepper at the stage when it is Mrs. Howell's turn. Then, when all the competitions are complete, the final decision rests with the judge.....Gilligan!

Gilligan meets his double, a foreign spy who has undergone plastic surgery in order to look like Gilligan (why, we're not sure!). Gilligan gets in lots of trouble as his double steals Mary Ann's pies, etc . . ..

A drab, plain-jane woman lands on the island seeking privacy. The girls give her a beauty make-over to lift her spirits, and she ends up looking like Ginger's twin. While the castaways were hoping to lift her spirits enough so that she would want to return to civilization (she has a boat, but has hidden the key), she ends up leaving them on the island and going back to Hollywood to attempt to assume Ginger Grant's movie career.