I remember when I played Ruby. Good times.

Does anyone ever relate Pokemon games to different points in their life?

I think it's part of the nostalgia for me. When I think back over past generations, and I try to remember the various regions and things that I did while playing, I also think about those points in my life outside of the game. Like, I really enjoyed Hoenn, and it's my favorite gen, technically, but I also wonder if that's partially because where I was at in my real life during the point where I played those games was a pretty good one. So I relate R/S/E not just to playing fun games, but also to the memories of that point in time, and the friends I had then that I don't see as much anymore. :> Hoenn has pleasant memories for me.

Gen 1 reminds me of being really young, and having a bunch of friends over to play the games, and I'm sure having a bunch of kids screaming about Pokemon all day long was obnoxious for my family. lol

Likewise, if I do go back and play a gen 1 game nowadays, it's not quite as fun, and it feels like something is missing from it. Cause I relate to a point where I was 20 years younger.

What are some of your memories?

I definitely feel the same way, Emerald reminds me of when I was a lot younger, and would spend a lot of my time playing Pokemon with my friends and at the same time I played Gen 5 when I was a young teenager, so B/W reminds me of those years of my life. Not to mention the countless holidays I've enjoyed playing Pokemon games, which are really nice memories too.

I mostly play FireRed rather than LeafGreen when replaying it because I like the regional exclusives better, but either one of the Gen 3 Kanto games brings me back to playing Pokémon for the first time. I think I got LeafGreen when I was... 5? or something? It's been a while lol, I played that game over and over again before even considering getting another one, and I still have a lot of fun childhood memories from then.

Yeah, every time I play Pokemon RSE and GSC, I remember the times where I played with my 5th grade class. We would trade, battle, and show off our rare pokemon together. With Pokemon Crystal, I always used to go to a babysitter's house and read up on bible stories before and after playing Crystal. With RBY, I remember playing them in a friend's house. He didn't like to share, but I didn't seem to mind~

Just remembered another great memory, I associate Crystal when I would get up early in the mornings on weekends to go and watch Pokemon on Sky. I was quite young then, and I used to love watching the Johto Journeys and playing Crystal at the same time :)

Luna said:

Just remembered another great memory, I associate Crystal when I would get up early in the mornings on weekends to go and watch Pokemon on Sky. I was quite young then, and I used to love watching the Johto Journeys and playing Crystal at the same time :)

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That is really cute ahaha c:

When I was 13, I used to come home from school to play LeafGreen, Crystal or Emerald and sometimes watched Johto Journeys on Toonami. Since I wasn't interested in Pokemon between 2001-2005, that was first time I watched that series.

I remember the fun I had at the 10th anniversary event in 2006. It was the first Pokemon event I ever went to and I still have the Raikou I got from it in my games.

When I think of the time when we first got our family dog just after Christmas when I was 14, I associate it with the Pokemon games I played from my birthday and Christmas. For my birthday, I got a Gamecube with Pokemon Colosseum as well as Mystery Dungeon: Blue Rescue Team and I then I got XD: Gale of Darkness for Christmas. I remember one day, I was playing XD while the puppy was sleeping on my lap. I also remember coming home from school to play Mystery Dungeon while keeping an eye on the puppy.

Diamond/Pearl reminds me of summer 2007. I was hoping Pearl will be the first Pokemon game I get on release day, but I was disappointed when I had to go on holiday in Costa Rica with my family during the release day (I found travelling abroad too overwhelming when I was young, but I really enjoyed the holiday in the end). The day after I got back, I picked up my copy from GAME and spent the whole of August playing it. During that time, TRU held an event where you can get Mew.

I tend to associate Yellow, which was my first Pokémon game, with my 6th Grade year (first year of middle school), since I got that game for Christmas that year. I began coming up with headcanons regarding Pokémon for the rest of that school year (1999-2000), and into the next few school years, and even drew a bunch of pictures based on those headcanons. (I even imagined a few of my own Pokémon, and drew a couple of them, but unfortunately, I don't have those drawings anymore.)
For quite awhile in the early 2000s, Pokémon seemed like an escape from real life for me.
Similarly, I tend to associate Gold and Silver with 7th Grade, when 7th and 8th Grades were held at my district's high school due to the middle school being remodeled that year (2000-01), but my memories of those games aren't as vivid as those of Generation I.