- Accidental Innuendo: Dobie wants a girl who's creamy? Okay...
- Adaptation Displacement: The show is far better remembered than the original Max Shulman stories it's based on, or the movie The Affairs of Dobie Gillis.
- Expy: It's easy to read the main characters as Expies of the main cast of Archie Comics, which predate the series by eighteen years and the original books by four years. Dobie = Archie, Maynard = Jughead, Zelda = a more Adorkable Betty, Thalia = Veronica, and Milton = Reggie.
- Hollywood Homely:
- Zelda. She was far more Adorkable.
- To a lesser extent, Dobie himself. He's a nice, funny, and good looking guy but can't land himself a girlfriend.
- Ho Yay: Dobie and Maynard, given how close, dedicated and protective they are of each other. Some episodes would end with Maynard insisting that Dobie doesn't need a girlfriend as long as he's got Maynard.
- Retroactive Recognition:
- Kids born after 1970 will wonder why Gilligan is such a stoner. Bob Denver was famous for being Maynard G. Krebs before landing his infamous role.
- Not to mention Warren Beatty and Tuesday Weld as Milton and Thalia.
- Seasonal Rot: There is a noticeable drop in quality during the second half of season 2 when Dobie and Maynard enlist in the army. Seasons 3 and 4 are also thought to be inferior to seasons 1 and 2, although praise is usually given to the episodes that feature Zelda or Chatsworth.
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