* EarWorm: The RealSongThemeTune "Wishing for a Sail" by Dig Circus.
* FanPreferredCouple: Caitlin/Eric had a bit more support than Caitlin/Will.
* SeasonalRot: Many viewers thought Caitlin spent way too much of season two mooning over "bad boy" Will, in contrast to her tough, independent characterization in season one.
* WeirdAlEffect: ''Series/TheAmandaShow'' had a pitch-perfect parody of Caitlin's Way in ''Moody's Point'', which became very popular and was seen as a general parody of TeenDrama as the show was forgotten.
** ''Moody's Point'' was a much closer parody of Series/DawsonsCreek than it was of Caitlin's Way. The teaser for ''Moody'' even acknowledged this.
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