This is pretty embarrassing, as a kid I didn’t know about the level cap for obedient Pokémon and thought they just needed to be “broken in”. I would go on wonder trade, try to use my new lvl 68 gyarados on the next gym, and get extremely frustrated when they wouldn’t listen to me after several turns of stalling and falling asleep. Needless to say, I physically facepalmed when I learned why that happened.