I Am Not Okay with This (2020– )
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Probably current times. Though they are really going for an 80s/90s vibe with the clothes/cars/music/vhs and cassettes. Most likely just an artistic decision.
Sydney's booth at the diner has 2013 scratched into it.
Also, in season 1 episode 5 during the test, the teacher is reading a Popular Mechanics magazine for the 2019 Tool Awards published for June 2019.
It's quite possible deliberate choices were made to stage Syd's home with dated furniture, decor etc. to indicate her family's socioeconomic status. For fashion, everything old is new again at some point.
Dina has a cell phone while they are in the diner, I believe in episode one. Also, when the kids need to get the "tape" of what happened in the library, it is on a USB drive. However this show, based on fashion, music, and cars seems to take place in "any time". Choosing a small, dated looking town in PA seems to ad to this effect. Edit