Whoops guess I never replied for this

Few examples I can think of in the show:

• There’s many technologies shown were more impressive for their time. Jian Yang’s hot dog/not hot dog app i.e. the joke that we were mislead to believe, that it would identify an object and identify what it is would genuinely have been more impressive at the release of the episode and not so much now. There’s things like drones, AI where at release you thought “wow imagine a future with these” compared to now where the future for these has actually arrived.
• IIRC the last season starts with Richard Hendriks testifying in court, and it’s a big reference to Zuckerberg doing the same for I think the Cambridge Analytica scandal? The moment would be lost today
• Lots of things around the opening sequence changed per season as companies got acquired and died, you saw that and said “Oh yeah that happened!” vs now you might just say “Oh yeah. that happened”.

Then there’s things not in the show that would date itself like the shift to remote working post pandemic, or the massive focus companies are giving mobile now which again wasn’t as big as at release of the show. I bet Gavin Belson trying to micromanage remote workers or something around the short form video craze we have would have been important plot points if the show came out now.