The Gym Leader battles that surprised you the most upon your first challenge

[Almonds]

Everyone has their first, and perhaps to get through the story, many have avoided guidelines and spoilers, turning to NPCs in-game to figure out what to do next.

The Gym Leaders are one of the biggest challenges you face, and the question is:

Who surprised you the most when you battled them?

There are moments when you just yell out a swear word because you had been completely unprepared for a certain pokemon, or a certain move.



There were quite a few for me, but I should say Fantina because I didn't know about Aftermath and was shocked when my pokemon died when I KO'd her Drifblim, and Roark because I didn't know Cranidos had such a high attack - one Headbutt cut over half my HP ;_;




And no mentions of cut scenes because I know if I allowed that, everyone's going to talk about Elesa's B2W2 cutscene. Nope, not that. I mean battles.

 

[Jammy2A]

well, Whitney in Johto was a surprise.... at the time I didnt what rollout did.... other than that I can't really think of a gym leader that really surprised me

 

[Anser]

Cilan ¬¬ Come on, it's the first Gym Leader. I was definitely not planning having to fight him four times.

 

[ZACH ATTACK]

Brawly on Emerald and Cheren on B2. The 1st one of those is because I was a noob, the 2nd because I was being stupid. As far as I remember, the only 2 gym leaders I didn't beat on my first try.

 

[33Whimsicott33]

"Maylene is about to send out Lucario.

-Wait, isn't that a legendary?"

It happens when you're one of those to go on a media blackout for the new generation.

 

[Chiss]

When I was a about eleven I played crystal for the first time. I kind of underestimated Whitney because of her pink gym and trainers with Sentret. Then she OHKO'ed my Quilava with one hit. -.- I was shocked.

The twins in emerald surprised me. I had a level 40 Swampert so I thought that I would be safe. Enter Solrock's sunny day/solar beam.

 

[boabiol]

Whitney's Miltank and Lenora's Watchog. 'Nuff said

 

[Infinity Mk-II]

It doesn't count, but Blue being a Gym leader was a pleasant surprise.

More on the topic...

Bugsy's Scyther actually putting up a pretty good fight in both generations, sweeping with Fury Cutter the first time I saw it, and it using U-Turn efficiently.
Wattson's Manectric being too strong too, OHKOing Shock Wave.
Winona having an Altaria. I didn't even know what an Altaria was other than "oh god was that just a Dragonbreath?"
Juan rematching you in a Double Battle.

... And that's about it.

 

[Ziggy Stardust]

Mil......motherf**k*r...tank!

 

[Ghetsis-Dennis]

Lenora, Cheren, and Skyla (in BW2). Lenora's Watchog proved to be a worthy adversary, and I was left with a Purlion to defeat it. Cheren's Work Up spam and my underleveled Pokemon caused me to SR. Skyla messed up my strategy when her Swoobat OHKO'd my Vibrana on the first match, and it took down my Scolipede.

 

[Proxima Centauri B]

Most of the Hoenn gym leaders I thought would be easier. I found Flannery particularly difficult, I thought it would be easier that that but that Torkoal messed me up. >.<

 

[Poke Prophet]

That's a tough one. I've played through so many times on each gen I've lost count. But from what I can remember from my first playthrough of ruby I remember being surprised by the double battle with the twin gym leaders, not only by the double battle but by the fact that Lunatone and Solrock seemed so bulky at the time.

But one that definitely threw me was when I replayed my red version, Sabrina uses a Venomoth. I didn't think anything of it at first but now I realize that Venomoth is poison/bug, no psychic typing.

 

[Phantump]

Roxanne's Nosepass was by far my greatest surprise. I was using a Mudkip that was on the verge of evolving, and I still couldn't even 2HKO that Nosepass with its defenses.

 

[AshK]

Lenora always tend to ko a pokemon of mine due to friggen retaliate after I beat her first pokemon. If I do a nuzlocke rock type is a good thing to have to absorb that.

 

[Sweet Solitude]

The one that really surprised me was Juan in Emerald. That Kingdra he has with ice beam, smokescreen, dragon dance, and surf was ridiculously unfair. If you couldn't beat it in the first few turns, you were done for.

 

[Plush]

I am going to repeat what a lot here have said.
Whitney and her Miltank...

 

[Gengarzilla]

I really had no problem with beating down Whitney, mainly because the Monferno I had traded round ended up a female. All my hate goes to a certain annoying psychic duo... It took me at least five tries to get past them, even with two dark types. Juan's Kingdra was also pretty unfair.

 

[ImperialSunlight]

Chuck in Gold was surprisingly difficult. That Poliwrath. ~.<

 

[Risa Katou]

BUGSY. So very much. I thought since he was using Bug-types, he was going to be easy. Apparently not! I cannot even BEGIN to count how many times I died to that Scyther.

 

[Master Simm]

I had no trouble with Clay in B/W. None at all.

BLACK 2 ON THE OTHER HAND...