Gen II & IV: Whitney

Whitney has always been difficult, regardless if I went Cyndaquil, Chikorita, or Totodile (I usually do Cyndaquil but have played through with all 3 starters at least once). I once took 3 weeks to beat Whitney when I was younger, and I think I had Chikorita that run.

 

Spoiler

Kind of like LoZ OoT's Water Temple, I actually never paid attention to Whitney being difficult despite how much of a meme each of these thing's became for their disproportionate difficulty. I don't know how I got around it way back in Gen 2 or even Gen 4, I probably just did my best with Croconaw and made it eventually without any psychologically scarring. I mostly find it funny how everyone else goes on about the difficulty of it while I can't even remember doing it.

If anything, I've actually learned to have an intense appreciation to her tactic. The few times I've won in competitive battling have been because of Ice Ball and/or Rollout. My hat is off to you, Whitney, for discovering my favorite technique before I discovered it.

 

Let me think... I usually trained excessively, and I remember being able to get one of the Eeveelutions before battling (thanks to Bill giving you an Eevee when you found him on the left side of the city). I fond her fairly easy with my amount of training, but I would still call her difficult. She was nothing short of annoying, and I was always on the offensive. If I was lucky and poisoned her, then I was glad since that would do its own work while I did my own in trying not to die. But other than that, I found it a fun battle overall. Quilava and Umbreon were my lifelines during that battle, as opposed to my more common Bug and Normal attackers.

 

Doesn't Bill only show up in Goldenrod and give you the Eevee after you bump into him at the PokeCentre in Eucreteak, which you can only reach after beating Whitney? Or is that just HG/SS?

Anyway, I remember losing my first time against Miltank in Silver. What I didn't know back then was that Defence Curl doubled the power of Rollout, so it took me awhile before I managed to beat her - I think I had to resort to the traded Machop in the Department Store and overlevel him. When I got SoulSilver, I was a lot more knowledgeable (especially having written a walkthrough for Emerald and destroyed Platinum), so clearing Whitney was a fair bit easier. However, even with all that said she was still a challenge, and has become the standard that I measure all Gym Leaders against (the reason Sabrina doesn't fit this is because, back in R/B/Y, Psychic-types were broken, but by the time FR/LG came out I had a method for cheesing her fight).

 

At first, I failed spectacularly against her. So I did some research and discovered the Fighting type weakness. Since then, she was no trouble at all.

 

I...honestly don't remember my first encounter with Whitney. Back then I had the brilliant idea of using the Cyndaquil family in 95% of all battles, causing me to be way overleveled most likely against her in Crystal. Though even years later in my first and only playthrough of SoulSilver, I had no problems with her thanks to the same strategy.

 

Whitney works as a perfect noobslayer. Any kind of strategy can win against a mon that just spams the same attacks over and over, but new players will have trouble against such thing because of Miltank's relatively high stats.
It is sad that, as almost all players just play it easy and keep the switch mode instead of set, Miltank won't usually get to revenge kill anything

 

Legit in Crystal I had to level my Quilava to evolution to take her, it was hell because the stupid thing stopped listening to me after it got too strong.
She was easier in HGSS I find?

 

I battled her Miltank with a Togepi and used Metronome. It rolled Fissure. I won.

._.

 

My battle with her was really easy. First in HG/SS I steamrolled through her with just a Croconaw, and recently I played the original games and I defeated her the exact same way I did the first time.