When the Castways overhear an announcement about a beauty contest on the radio, an argument starts between the Skipper, the Professor, and Mr. Howell about which of the island's ladies is the most beautiful. The girls happily take to the idea when Gilligan suggests a beauty contest of their own, and as the only other man on the island, the hapless first mate quickly finds himself caught between the others, who are determined to sway the tiebreaker.
This episode includes examples of the following tropes:
- Agony of the Feet: When the Skipper asks to talk to Gilligan alone, Gilligan sends Gladys away. As she leaps to the ground, she lands on the Skipper's foot.
- Beauty Contest: The Castaways hold a contest to decide "Miss Castaway", the prettiest woman on the island. What do you think — Ginger or Mary Ann or Mrs. Howell?note When the Skipper, Mr. Howell and the Professor confiscate Gilligan's notes to find out who was leading on points, they find that all he did throughout the contest was play Tic-Tac-Toe... and lose every single time.
- Chekhov's Gunman: Gladys, an island gorilla, appears in multiple joke scenes. Gilligan brings her back later so that he doesn't have to choose one of the female Castaways as winner.
- Delayed Reaction: While Gilligan is talking to Gladys about his problem, Mr. Howell arrives and takes her spot. Gilligan laments that he wishes someone could tell him how to resolve his judging dilemma and Mr. Howell tells him he'd be glad to do so. Gilligan answers "Thanks" before his eyes widen and he turns to see Mr. Howell.
- Enemy Mine: After each of them sabotages the other's favorite contestant, Mr. Howell and the Professor team up to sabotage Ginger during her musical number in the talent event.
- Instantly Proven Wrong: When Mary Ann's soft-shoe dance is ruined by a glue puddle, the Professor accuses Mr. Howell of sabotaging her. (The Skipper had been onstage helping him with the phonograph, making Mr. Howell the likeliest suspect.) Mr. Howell denies it...and promptly gets his gluey hand stuck to the Professor's suit.
- Poor Communication Kills: The Professor tells Gilligan not to help him with the fishing rod, but he doesn't tell him he's using it to help Mary Ann, not for fishing. As a result, they pull off her swimsuit in the struggle.
- Sticky Situation: The Castaways hold a beauty contest between the three women. During the talent portion Mary Ann is to perform a dance routine, and Mr. Howell tries to sabotage it by pouring glue onto the stage. Mary Ann, of course, steps right in it, becoming instantly stuck and loses her shoe (which is still stuck in place in a later scene).
- Stripping Snag: To provide isometric exercise, the Professor has Mary Ann swim in the lagoon while he holds onto her swimsuit with a fishing rod. Gilligan arrives, and, thinking the Professor is struggling with a huge fish, tries to help. As a result, Mary Ann's swimsuit comes flying off, to everyone's embarrassment.
- Suspiciously Specific Denial: During the "charm, poise, and sincerity" event, Mary Ann gives a speech full of long words saying that her utmost desire is world peace. The Professor (doing the announcing) thanks her for an honest, selfless and unscripted speech.
- Take a Third Option: The Castaways hold a beauty pageant to name "Miss Castaway", and Gilligan ends up being the deciding vote between the three girls with some strong-arming from their supporting men. At the end, Gilligan grabs the Smart Ball and takes the fourth option by choosing an island gorilla as the winner, pointing out that "Well, to enter a beauty contest, you have to be a native, and she's the only one born on the island... besides, if I picked one of the ladies, I'd get in trouble." The other men find this reasonable, but it doesn't stop them from checking his notes to find out which of the human women he had given the most points. All they find are tic-tac-toe boards. Gilligan sheepishly says that he didn't want them to see that he'd lost every game.
- Tempting Fate: Gilligan says that he would get in trouble if he picked any of the women, but if he picks Gladys, he won't get in trouble. Gladys promptly picks him up and carts him away.
- You Have GOT to Be Kidding Me!: Ginger name-drops the trope when she hears the contest winner referred to as a "co-ed", snapping that she's been entering contests since Ginger's childhood.
