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Old January 21st, 2012 (3:55 PM).
Avori Adonis's Avatar
Avori Adonis Avori Adonis is offline
Join Date: Oct 2004
Location: New Jersey
Gender: Male
Nature: Quirky
Posts: 17,238
If remakes don't count, I'm going to go with my first playthrough of a game.

Gen 1:
Gym 1 - Brock: Brock was hard in Yellow because all I had was Pikachu when I first battled him.
Gym 5 - Sabrina: Since psychic types didn't really have much of a weakness in Gen I (you can say Gastly, Haunter, and Gengar, but since they're part poison, throw a psychic at them and they'll faint easily), she was really hard.

Gen 2:
Gym 3 - Whitney: Underestimating normal type Pokémon round 1. Miltank was just a powerhouse.

Gen 3:
Gym 5 - Norman: Underestimating normal type Pokémon round 2. That Slacking was just as much of a powerhouse as Miltank.

Gen 4:
Gym 3 - Maylene: I didn't know Lucario's typing when I first battled it in Diamond, so I lost to it a lot before finally going to look it up.

Gen 5:
Gym 2 - Lenora: Underestimating normal type Pokémon round 3. Retaliation and that powerhouse of a Herdier combination is deadly.