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Gen 4 was the best for me.
>Gen1
My older brother highjacked my blue to complete his dex and I was too much of a bitch to get it back.
>Gen2
Brother just kept all my trade to evolve mon, but I at least got to keep my game this time.
Had to start over twice because he convinced me to trade him my Tybrosion and start anew so we'd have Chikorita. Never got either back.
Haunter becomes bro tier mon.
>Gen3
Didn't know anyone else who had the game.
Brother is gone.
>Gen4
School friends are getting back into Pokemon.
Brother is no longer in Team Rocket.
Underground, contests, battle tower.
Trade evolutions for the first time. Platinum raising the fun. HG SS raising it even higher.
>Gen5
Some are falling back out of Pokemon.
Never get B&W2, but some friends do so resurgence a couple more times.
>Gen6
Most friends done with Pokemon or separated.
No DS compatible router. Still get together with brother to play Pokemon and chill from time to time.
Pokemon is pretty important to me, which is a bit sad, but it's been a big part of my life.
Least fun was Gen1.
Biggest challenge was Gen2 on account of my Rocket bro always tricking my dumbass and trying to beat the Elite 4 with no batteries when we were homeless.
Loneliest was Gen3, no one to play with.
Gen4 was most fun all around.
That was a lot of blogging, and I don't really have an excuse. pls no bully