Do you try to complete pokedexes prior to 6th gen?

My brother stopped playing Pokemon when Ruby and Sapphire came out, so I had no one to trade with.

I got pretty close in Ruby and Silver but unfortunately lost both files that I got close in. Soul Silver is probably the one closest to having a finishing Pokedex but even that is well ... missing a lot.

Completed the dex in every generation but it wasn't easy at all.

The worst was probably trying to get the Eeveelutions in Gen 1 before GSC came out - no-one would ever agree to trading so it took me and my brother replaying Red twice over to make the trade to Blue between us!
Feebas in RBE was sooo annoying to find.
Then there was the Feebas and Munchlax issue in DPPt... Ugh.

Since Gen 6 was released completing the dex has been so much easier so not really struggled with it since then.

I never used to during their initial releases but went out of my way to complete the Pokedex for the virtual releases of Yellow and Crystal. I even did my best to give them their ideal competitive movesets, egg moves and all. Not sure why since I have nobody irl to battle and you can't use wifi for those games but it was satisfying busy work for some reason. I'd love to be able to complete the Gen 4 dex too but it's not possible for me without cheating.

Black said:

I'd love to be able to complete the Gen 4 dex too but it's not possible for me without cheating.

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Yeah that's the unfortunate thing with trying to complete the dex for older games these days. If you missed the event(s) for the event-only Pokemon, then you're screwed when it comes to those. The only time I have ever completed the National Dex was on my Pearl, but in that case I had to use an Action Replay to get an Arceus and Shaymin (and probably a few others like Mew or something) to have all 493 registered as caught, as this was years after Diamond/Pearl's release. So like, it was completed, but not 100% legally.

That's why I wish they'd put mythical Pokemon in the base game more often like they did with Deoxys in ORAS. It might make them feel less special and more like typical legendaries but timed events just add less incentive to play through older games. Even if you're not a completionist who wants to catch every single Pokemon, a lot of the mythical Pokemon are popular so it's hard not to feel like you're missing out on important stuff. Some of the mythicals even have short side stories before catching them so that's even more content you'll miss out on if you didn't play the games during the right time period. Or if you didn't have wifi access until 2013 like me.

Sadly I couldn't because no friends, but thanks to Gen 6 I can, my dad has a completed pokedex pre-gen 7, but that was because of gen 6, he worked his butt off for it too.