* ApprovalOfGod: Or at least with the actors. Creator/MichaelSeater and Ashley Leggat were (and [[https://ew.com/tv/2020/01/21/life-with-derek-michael-seater-ashley-leggat-incest/ still are]]) huge Derek/Casey shippers. They even acted out a fanfiction for a podcast back in the day.
* TheCastShowoff:
** Creator/AshleyLeggat, who plays Casey, is a professionally-trained dancer, and the show emphasized this repeatedly in later seasons. The TV-movie ''Vacation with Derek'' even made a whole subplot out of this, casting ''[[Series/SoYouThinkYouCanDance So You Think You Can Dance Canada]]'' winner Nico Archambault as her love interest.
** Leggat is a triple threat entertainer. She is also a singer, having sung a few times on the show.
* DawsonCasting
** Played straight with Ashley Leggat who was 19/20 playing a 15-year-old, and with Michael Seater who was 18 playing a 15-year-old.
** This was averted with Daniel Madger (Edwin), Jordan Todosey (Lizzie), and Ariel Waller (Marti), who were all around their characters' ages at the time of filming.
*** Actually, Daniel Madger is four years older than Jordan Todosey, despite them playing characters that are around the same age.
* FakeNationality: American actor Creator/AlSapienza plays the Canadian businessman who wants to develop the lake in TheMovie.
* OnlySoManyCanadianActors:
** [[Series/DegrassiTheNextGeneration Lauren Collins]] as Kendra, Derek's first long-term girlfriend.
** Michael Seater, Creator/JohnRalston and Shadia Simmons had all before been featured on the Canadian series ''Series/StrangeDaysAtBlakeHolseyHigh''.
** Kate Todd, who played Sally, starred in ''Series/RadioFreeRoscoe'', another Canadian sitcom.
** John Ralston starred as Emperor Ming in the short-lived [[Creator/{{Syfy}} Sci Fi Channel]] adaptation of ''Series/{{Flash Gordon|2007}}''.
** Ashley Leggatt and Shadia Simmons also appeared in ''Series/AceLightning''.
** Before ''Strange Days at Blake Holsey High'', Michael Seater and Shadia Simmons also worked together in ''Series/TheZackFiles''. Ashley Leggat appeared with them in one episode.
* TheOtherDarrin: Casey's cousin Vicki appears in one episode in the first season and another in the fourth season, and is played by two different actresses who look nothing alike.
* PlayingAgainstType: Compare Michael Seater's role as Derek to the ones he played in ''Series/StrangeDaysAtBlakeHolseyHigh'' and ''Series/TheZackFiles''; Derek is completely different from Lucas and Spencer.
* RomanceOnTheSet: [[invoked]] By most reports, Ashley Leggat and Michael Seater dated during production of the first season before deciding they were BetterAsFriends, so a lot of the tension between Derek and Casey was not ''entirely'' a case of PlatonicWritingRomanticReading on the part of the writers. Given they're PlatonicLifePartners, they're also an example of AmicableExes.