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What was the hardest fight for you

I didn’t know it was strange to take 5+ tries on someone?????

I just probably built trashy teams with no balance and I didn’t care about stat moves or stats in general when I first started

Now I’m a lot better but it still takes me forever to beat certain people

I also think it’s partly cause of scarlet and violets open world do gym leaders in any order taht I accidentally skipped ahead and ended up in an overleveled gym
 
How the heck did I forget about the PLA Noble Pokemon battles? God, I hated those, save for Kleavor, Lilligant, and, weirdly, Electrode. Lilligant was my favorite--just the right amount of challenge to make it fun, but not expletive-producing.

The battles against Arcanine and Avalugg only solidified my hatred for real-time combat.

I didn’t know it was strange to take 5+ tries on someone?????

I just probably built trashy teams with no balance and I didn’t care about stat moves or stats in general when I first started

Now I’m a lot better but it still takes me forever to beat certain people

I also think it’s partly cause of scarlet and violets open world do gym leaders in any order taht I accidentally skipped ahead and ended up in an overleveled gym

You're not alone. I often have to fight multiple times because of all my compulsions. Even though I used a guide to take on everyone in the "right" order, I still struggled with Atticus and end up overleveling my Pokemon in response.
 
Having played Legends Arceus now, I can safely say, yup, Volo is definitely up there for me. Even right now I still haven't beaten him. I was usually already down to one Pokémon once he sent out Giratina so I was basically screwed from there . Half the fight is just me fiddling with potions and and revives. I hope to beat him eventually, but man the fight tests my patience ahaha

On the topic of Legends Arceus, the post game Kamado fight was also up there. Half of his Pokémon were tanks. It frustrated me so much I took a breather from pursuing him. It took me nearly a year to go back and finally beat him and progress to the rest of the post game story. And even then I basically cheated by transferring some of my stronger Pokémon from Home to finally take Kamado down
 
Sinnoh's Elite Four was the point I never cleared as a kid, with Bertha and Lucian being the worst of the bunch for my severely underleveled and not even fully-evolved team.

I only really managed to win the first four battles through luck and shenanigans (outlasting the opponents with a truckload of healing items), and even then, it was an effort that managed to span days. But I didn't account for my Pokemon running out of PP... I had been saving my progress in between each round, so by the time I made it up to Cynthia, most of my monsters' moves were drained and I had no Leppa berries on me to fix that. Once I realized there was no way out of that hole except losing and tackling the E4 again from the top, I chose to... erase my file and just start the whole game over, for some reason.

I never beat Gen IV until I got my hands on a copy of Platinum many years later. @~@
 
Ghetsis in B/W gave me a lot of trouble, especially his Hydreigon. I had to rely heavily on healing my team with Revives and Full Restores to beat him. his Hydreigon has Fire Blast to counter Ice and Bug types, as well as Dragon Pulse to counter dragons. Pretty much the only weakness it has is to fighting types. Took me several times though I managed to win. That battle was so painfully tough that it ruined the fun out the game.

I also struggled to beat Cynthia and Cyrus in Platinum, though mainly because I didn't have a well-balanced team. In addition, I think Morty's Gengar in Gen 2 was hard for me to beat because there weren't a lot of Dark types available early on in the game to beat him.
 
Kukui in Sun and Moon took me a stupid amount of times, probably because my team was horrible (I don’t exactly remember the team I used tho)
The team members I do remember were: Primarina, Bewear, (Alolan) Ninetales, Zygarde 50%, Lunala
I think I was under leveled outside of Lunala and Primarina (because you get Lunala at 55 and I swapped my team so much that Primarina was the only decently leveled one)
 
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