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Most frustrating moments in Pokémon games?

They surely revolve around Paralysis and Confusion. Also Bind, Wrap, etc. moves like that in Gen I. The RNG is very cruel, also in-game these statuses rarely effect the outcome of the battle, but instead frustratingly delay my victory.
 
status effects never working for you but always at max efficiency for the CPUS is a classic

Whitneys miltank in gen 2 is another contender for practically forcing you to level grind just to stand a chance

roaming legendaries are always a pain. Combo of being so hard to pin down AND hard to keep them in the battle (Why can they run when frozen)
 
Accuracy checks. Somehow when used by the NPC, the one-hit KO attacks like Fissure and Sheer Cold are no longer 30% accurate! Also, in a recent Tera Raid Battle using the one-shot strategy with one Gholdengo and three Steely Spirit Perserker, my Gholdengo's 95% accurate Steel Beam missed... We were wiped out. Steel Beam missed again on our second attempt.
 
Usually in gens 1 and 2, trying to grind for the Elite Four because the level curves are at their worst in these games. Gen 2 also made pokemon able to flee, which includes some of the newly added gen 2 mons like Teddiursa and Snubbull.

Other than that, always hitting myself with confusion for massive damage while the opponent barely takes any damage from confusion. And that's if they even hit themselves from confusion. It seems like whatever accuracy debuffs are given to your opponent doesn't matter, but they matter far more to you.
 
Catching legendaries. Stay in the ball. Mentions Dialga as the most memorable recent offender, as a specific case. Brought it to Struggle time twice before catching it on the third try.

Route 13 in X/Y. Remembered the actual route number as proof. Needs to wait for the proper wind to get on the rail. Occasionally hits it a little too slow and simply falls off the rail. Also deals with random encounters harassing you that cannot be repelled. Includes Dugtrio (with potentially Arena Trap) at a 40% encounter rate.

Seconds roaming legendaries. Hates dealing with those. Constantly plays the lottery to make them move to the right area.

Probably fourth on the list: setting up with buffs, then getting criticaled at the last moment. Applies to Tera Raids in particular. May have had to reset multiple times for a decent team too. Only falls fourth on the list due to understanding decent odds of getting criticaled at some point. Runs that risk with that strategy (barring handy abilities that prevent it). Points to a recent time with Krookodile versus Rillaboom getting criticaled on the last hit before Terastallizing and Power Tripping.
 
I remember getting to the very last level of a Super Battle challenge at the Battle Maison, and losing to the Chatelaine as one of her legendaries started spamming double team- I think it would have been the genies, but it's been some years. I was so mad after 50 battles of hard work to have it all wiped away, based because of thr final boss using completely luck-based moves that require no skill.

Something that also makes my blood boil is an encounter on the Battle Subway in Black and White 2 with an random npc's Armaldo. I sweeping through their team and this was their last pokemon. I had all three of mine still alive and in good conditon. Each one was faster, and had a super-effective move against it. But this demon of a pokemon had a quick claw, and it activated EVERY single turn, and then proceded to land 3 stone edge attacks with crits. This one of those events that convince you that there is no cosmic justice.
 
I dread trying to catch a legendary with recover.

Specifically, thinking of Lugia. It's a long and tedious fight.
 
Anything involving bad RNG really, especially evasion/accuracy related stuff. Play Rough has 90% accuracy and I once had it miss 4 times in a row while my opponent landed 3 consecutive Focus Blasts..... 🙄

First time fighting Ultra Necrozma was frustrating too as none of my team first time round could handle it and I was forced to re-fight it using Toxic stalling. Blind playthoughs have their downsides I guess xD
 
Having to spend hours and hours training an underleveled team (compared to the gym leaders' team you have to face before moving forward) by grinding wild pokémon who themselves are 10 or more levels below your team's).

I dread trying to catch a legendary with recover.
Specifically, thinking of Lugia. It's a long and tedious fight.

How about a Legendary who likes to use Destruction without moderation ?
(Yes, you, Insurgence's Genesect!)
 
When you lose your streak in a battle facility when you had gotten so far into it.

Like... this is so frustrating. I worked hard to get that far...this especially applies to the Battle Pyramid in Emerald. I remember this one time I had gotten all the way to Brandon and lost.
 
HMs. Need I say more? I call them "horrible moves." I mean, Fly is pretty decent, especially for in-game playthroughs on a strong Flying-type physical attacker, and Surf is pretty good as well on any specially attacking Water-type Pokémon. Waterfall is also a good move for a physically attacking Water-type Pokémon. However, the rest of them completely suck and simply take up space when you want to give your Pokémon good movesets. I swear, at one point, I literally had to teach my Starmie all the Water-type HMs, which was Surf, Dive, Whirlpool, and Waterfall just to complete the game. You need a move deleter to delete them. If only you knew how bad that sucks. It's crazy! CRAZY! I'm so glad that Generation 7 did away with those horrible moves for good.
 
Having to spend hours and hours training an underleveled team (compared to the gym leaders' team you have to face before moving forward) by grinding wild pokémon who themselves are 10 or more levels below your team's).

Yes, this has happened to me lately since I beat Pokémon Diamond and now get closer to beating HeartGold. Which is strange considering I challenge all trainers in each area I visit. Maybe I should avoid using repels at all. I think I just may be bad at these games, even though I enjoy them overall. Well, now on to leveling up my team for a few more hours. Thank you friend.
 
Yes, this has happened to me lately since I beat Pokémon Diamond and now get closer to beating HeartGold. Which is strange considering I challenge all trainers in each area I visit. Maybe I should avoid using repels at all. I think I just may be bad at these games, even though I enjoy them overall. Well, now on to leveling up my team for a few more hours. Thank you friend.

I'm pretty sure there's nothing wrong with the way you play those games, Heart Gold is a very slow, grind heavy game. (I believe at least Platinum was as well, if not quite as much) If you ever play any of the newer games, even as early as Gen 6 on the 3DS, you'll notice that there isn't nearly as much of a slog of necessary level grinding to go through if you battle every trainer. Which is even more noticeable in the Switch Pokemon games by the way.
 
Yes, this has happened to me lately since I beat Pokémon Diamond and now get closer to beating HeartGold. Which is strange considering I challenge all trainers in each area I visit. Maybe I should avoid using repels at all. I think I just may be bad at these games, even though I enjoy them overall. Well, now on to leveling up my team for a few more hours. Thank you friend.

I did not have much of a long grind issue when I played Heartgold, for I used the following Pokémon team :
- Typhlosion.

I soloed the game, League included with him! ^^
Less recently, when I went on the third generation, I did the same thing on Ruby with Swampert!
 
I'm pretty sure there's nothing wrong with the way you play those games, Heart Gold is a very slow, grind heavy game. (I believe at least Platinum was as well, if not quite as much) If you ever play any of the newer games, even as early as Gen 6 on the 3DS, you'll notice that there isn't nearly as much of a slog of necessary level grinding to go through if you battle every trainer. Which is even more noticeable in the Switch Pokemon games by the way.

Yes, now that you mention it, I do remember having no problems at all regarding this issue with X and OmegaRuby. I believe leveling up in B&W was also less grindy with Pokémon like Audino, if I remember correctly. I think you are right, maybe this is something innate to gens. I through IV at least. Thank you friend.
I did not have much of a long grind issue when I played Heartgold, for I used the following Pokémon team :
- Typhlosion.

I soloed the game, League included with him! ^^
Less recently, when I went on the third generation, I did the same thing on Ruby with Swampert!

That is amazing, Typhlosion truly is great. I might have to try this in the future. Thank you friend.
 
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