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I HATE Whitney. At the time I battled her I only had a Quilava and a Natu. My Natu's only attack was Night Shade :/ Big help that was. But I got a TM for Aerial Ace and he evolved into Xatu, so the second time we battled her, he was an extraordinary help.
Battle wise, I also find Morty difficult. I usually don't have any super effective moves against him. But, as stated earlier, when I get there I'll have a Pyschic TM on my Xatu and I think that gym will breeze by pretty easily.
I can't help but be amused that when the gym leader levels were released a lot of people were all 'WHY IS WHITNEY SLIGHTLY WEAKER EVERYTHING SUCKS NOW SHE WILL BE TOO EASY'. Clearly not the case for a lot of people in HGSS, heh.
I haven't had a gym leader that is consistently too hard for me, but some have been annoying to beat due to hax or me doing a monotype challenge. Bugsy in particular with U-turn Scyther is NOT FUN when you only use grass-types. =p Brawly at times liked to use Double Team Hax and I always found Surge to be annoying if I didn't have a ground type/EQ user for that same reason...
Whitney and Clair
One is a crybaby, the other is a sore loser.
Plus I spent so much time to KO that Miltank. With Clair her kingdra was faster then my Dragonair, which my entire tactc for that battle was based around. I wasted all of my max reveives on her
Whitney hasn't really concerned me this generation. I remember hating her in my Crystal days. I don't know whether that Miltank's moveset has changed in the meantime or my battle style, but she's definitely less difficult.
Right now though, Chuck is an irritation. Trying to take his Primeape down with a Flying type is nearly impossible. He forces you to depend on inflicting status conditions.
As everyone else has stated, Whitney always gives me a bit of trouble... her Miltank is simply annoying with the combination of moves it gives... and milk drink - ugh.
Other than that, the only gym leader who gives me pain is Jasmine. I know all her pokemon are steel type, but my Typhlosion usually can't take the earthquake from Steelix very well. @_@
Whitney and Clair.
I found Whitney difficult (I dislike that Miltank) and the way Clair responds to the player defeating her seemed pretty petty, that and her Pokémon kept beating me the first time around. xD