Happened twice, both to my #1 games. Tried Chrono Trigger as a kid and didn't like it, then came back and played it as a young adult and was like... damn... this is an actual treasure.
In 2015 I tried FFXI due to the XIV crossover event, and I could not get past the eccentric and clunky UI and the pacing of the combat. I tried again a couple of years later and committed to finishing all the stories. It became my new #1 and I think genuinely one of the best games ever made, in terms of revealing and pushing the artistic potential of online games, and games in general. Actual masterpiece and a massive innovation, and unlike Chrono Trigger I think the lessons are going to be a lot harder to learn and replicate.
I get the feeling that "Techdirt" may be a bit biased.