It kinda happened for me with Fallout New Vegas. I was maybe 11 and never played anything from the series. I spent my time killer hobo-ing my way through but I always felt like I was missing something, then I started reading negative opinions about it online and got influence by that, so I dropped it. After some time I played Fallout 3, liked and thought it was much better than New Vegas and decided to give NV another shot (I was at 12 or 13 by then). I loved it to the point where it is probably on the top of my emotional top 10. It got me into 50s/60s music, got me interested in politics and ethics, made me become a fan of science fiction and old school RPGs focused on story and a variety of approaches. Really a fantastic game

The first Dark Souls. At the time I had played Demon's Souls, but didn't really play games for the challenge so I was very much not used to those types of games. Was also a diehard FPS player.

But a good friend, the same one that introduced me to Demon's Souls, gifted me Dark Souls. It was a game a genuinely enjoyed, but couldn't quite find my groove. I'd create a character, get to a certain point, then feel lost or too frustrated to proceed. So I'd stop playing for a few months, then pick it up again and roll a new character.

This trend repeated for a while, and I DID progress farther every time. Eventually, I hit a wall with one of the bosses and raged quit. So fast forward to my inevitable return to the game, instead of starting over I just went right back to that boss and tried again, and again, and again... and actually won?! That was the moment I feel like my gaming potential was awakened.

From Software fanboy, but also truly invested in a good challenge.

Unrelated, but I'm polishing of Nioh 2 now with NG+ and the DLC

I've never been able to have Skyrim or Witcher 3 click for me, despite trying a few different times (because so many seem to regard them as gold standards of action RPGs, a genre a do like!)

But, to answer your question, for me its probably Stellaris (and, through that, many of the weighty 'paradox games).

I'd always liked games like Civ (Sid Meier's Alpha Centauri being the first 4x that grabbed me, back in the 90s). But, 'Paradox games' were something I tried a few times, and bounced off of every time. They're just a different beast, in terms of 'weight'.

But, after having tried Stellaris and bounced off of it, I got talked into playing it multiplayer with some of my friends who play it more regularly, and having a knowledgeable person there to explain some of the weirdness and strategy to me made it all click.

And once I got that down, Crusader Kings and Victoria now were like, understandable to me. Though, I do think Stellaris is my favorite out of the bunch.

Stardew Valley. I pirated it because I really didn't think I would like it, but was curious about all the positive buzz that was going on around it. Played for maybe 45 minutes and decided that it wasn't for me. I think it was two weeks later that I picked it back up again because some article wouldn't stop singing it's praises. Start playing, look up, 4 hours had passed.

So I bought the game and proceeded to put over 200 hours into it.

Then I bought it on Switch and put like 160 hours into it.

Then I bought it on Mobile and put like 60 hours into it.

Never thought I'd click so well with some silly farming game.

The first time I played Jedi Fallen Order, I got through the tutorial mission, went 'Eh' and put the game down. Went back a year later and had an amazing time. Can't tell you what it was that changed.

Monster Hunter. I first tried it on the wii u when I was honestly too young to really comprehend what was going on and bounced off. Years later I picked up MHGU and MH World and got basically addicted. Now I own almost all the games physically, as well as picking up a 3ds and Vita so I could play the psp and 3ds games on the go.

Actually yes! Days Gone took me 3 reinstalls to get into it. I think I just pushed through the start. I ended up enjoying it I dont know why it got all the bad press.

Same happened for me with Deus Ex Human revolution. Back in 2012, I just didn't understand the plot and the atmosphere of the game, and wasn't a fan of the decision-making system. Last year, I plugged in my dusty PS3, started the game and I just had all the keys to a better understanding. Adam Jensen is a charismatic character and the scenario makes you want to go through the whole game in a row

When I first played Dwarf Fortress, I thought it was the dumbest shit ever because it was taking so long during world gen, I thought that was the game and it was like an ASCII Progress Quest.

Then it took some time to get used to the terrible interface it had pre-Steam version.

Now I acknowledge it as one of the greatest games ever made.

I had a similar experience with The Witcher, but the first one. Bounced off the game twice. Third time was the charm. I fell in love with it and then ended up playing the other games in the series as they came out. I'm not sure what made me keep trying, but I'm glad I did.

Long before that, when Morrowind was released, I couldn't quite understand it. I had grown up on JRPGs, and the openness of Western RPGs was confusing. I kept trying and eventually fell in love with it too. This opened up a whole new genre for me.

XCOM: Enemy Unknown had a similar effect for turn-based strategy games and Elden Ring for Soulsborne games. I'm still looking for the games that will open my eyes to several genres. I occasionally try games in genres I don't typically like in hopes this will be the one. It's really cool to have that new door opened for you.

Morrowind, I played it near release and had no idea what to do or what I was doing. Then I played it a year or two later and played it for weeks straight.

CK2 also took a bit of learning to get used to.

Valheim, i stopped playing after 5 minutes 2/3 times and then i just gave it another shot and played it for 30+ hours

Vampire Survivors. I did like it in the beginning, but I started to get bored since I got stuck in the first map. I uninstalled it for a while then I installed it again last week. I've been playing on and off again, since I was basically just trying to get a lot of coins. I managed to reach level 20 and unlock the second map, then yesterday, I reached 27 minutes in the second map and now I'm addicted to it lmao. I got the magic wand without cooldown on that playthrough, and it was so satisfying to see everything just dying.