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Regrettable starter choice

I wish I had gotten Lets go Pikachu instead of Lets go Eevee because Pikachus stab electric moves are way better than Eevees coverage moves since Lets go has a wide variety of early game pokemon with all different types at the beginning and mid game + Pikachu has better coverage moves for its type.
 
I don't think I've regretted any of my starter choices.

Yeah, there's some bosses that are harder to beat than others, but there are always going to be other battles where the starter will get to shine. The good thing about this series is that even if you have a starter who's not that useful, there are always other Pokemon there to cover its weaknesses. So even if I pick Chikorita or something, it's fine.
 
Piplup for me. Normally I choose Chimchar (given Sinnoh's lack of Fire Mons), or, on occasion, Turtwig, but I tried Piplup once just to see how it fared in Pearl. Especially since the anime was big on the Piplup line. It... didn't work out too well. Sure, Water/Steel is a great combo, but the regal bird just couldn't cut it for me. Later gens were much kinder to the line, but at the time it just didn't have all the needed tools to be useful. As a result, I usually let Barry have it in other playthroughs, as beating it up is more fun than running one. So, yeah, I regretted Piplup quite a bit and went back to my usual standby of either Chimchar or Turtwig, usually the former (again, thanks to the lack of Fire in Sinnoh).
 
Chikorita. Having to deal with Falkner, Bugsy and Whitney in quick succession + a badly translated game (my parents didn't know the cartridge was fake) made for a pretty miserable playthrough.

It doesn't help that that hack for some reason decided to replace the Super Nerd that had Magnemites in the Goldenrod Underground with a team comprised of a Lv28 Nidoran♀, a Lv28 Nidoran♂, a Lv30 Nidorina and Lv32 Nidoking. I have no idea why that happened.
 
One time I picked totodile in a soul silver nuzlocke and regretted it immensely because every time I had to fight Silver I had to deal with is brick wall of a Chikorita. Nowadays if I do a run again I will be picking Cyndaquil or Chikorita specifically so I don't have to fight one again.
 
Treecko.

Fricking Treecko.

Holy hell it is horrendous. If you're like me and didn't like to use limited use TMs, you were just hosed with this miserable excuse of a Pokemon. It's stuck with Absorb for half the game. A pitiful base 20 damage attack. And even if you use that Bullet Seed TM, it's not much better. It gets even worse, though! All three Gen 3 starters get a move after evolving. These are of the secondary type for the other two, but Grovyle doesn't get one. Instead it gets...Fury Cutter! A move that's somehow even WORSE than Absorb! I have never once used Treecko to the end in the three times I've picked it. Not once.

Then you have Snivy. Mother fudging Snivy. Do you like Grass? Well here's a bunch of Grass moves for your Grass starter and when it evolves you get even MORE Grass. Smugleaf's movepool is laughably limited compared to the other two where I'm convinced it's a joke. Even Gen 2 Meganium got Body Slam at a reasonable point, and if you somehow survived the horrendous early game Sceptile got decent with TMs and Leaf Blade. Smuglord? More Grass. And the best thing you get besides that is Aerial Ace.

These two were so atrocious and underperformed so badly I henceforth never pick Grass ever in a Pokemon game unless I've exhausted the other two options. Or if it is Torterra, the only one I've never regretted at any point.
 
Not really, since pretty much all starters have good stats, and I like team building so I tend to have at least another main member of my party early on, and I try to compensate the shortcomings of the starter with such members.
 
the closest one would be chespin, if only because i just... was (and still am) not a fan of chesnaught at all. @__@ i don't think i've had a terrible experience with it or anything, i just wasn't a fan of its design so going through kalos was definitely less than exciting for me because of it.
 
Rowlet in USUM. It was absolutely terrible. The entire team pulled its weight and this thing couldn't stay alive for the life of it.

Never again. Should have stuck with Popplio or went with Litten.

I was in a very similar boat. I was going to use Rowlet in another playthrough of SM before USUM came out, but I ended up not having the time. So, I used Rowlet for my UM playthrough and that was my first mistake. It's adorable and has cool evolutions, but I hardly used it. Honestly, my entire UM team was just not the best. Only my Ampharos could actually take a hit, and no one did lotta damage either.

__

I also seem to have issues with several of the generations, except for 3 and maybe 6, where I like 2 of the starters pretty equally so when I start a new playthrough I'll be in the mood to play with one, but then find sometime early in the playthrough I wanted the other one. This is actually one of the reasons I haven't gone back to my Platinum team yet because I feel like I'm too far in to reset, but I'm just not sure if Chimchar was the right choice.
 
Another one disappointed with Rowlet here.
I always pick the Water starter for my first playthrough of the first game of every generation. So for Sun (the first game I picked) I chose Popplio and I was super happy with Primarina.
But then I chose Rowlet for Moon and... I ended up boxing it. It is a terrible, terrible pokemon. Bad movepool, bad stats, bad everything. It's a shame since I loved Decidueye.

And then the other disappointment was Sobble. Like I mentioned, I always choose the Water starter for the first playthrough of the new generation. But Inteleon is super bad! I hated it! I regretted choosing Sobble and wish I had gone with Scorbunny instead.
 
I believe, for a playthrough of Y, I originally went with Fennekin. However, I regretted not using Chespin (I had used it in an earlier playthrough in X--the cartridge of which got destroyed) so I wound up boxing my Fennekin and trading for a Chespin to use.

I was also disappointed with Sobble... though I didn't really use it for my Sword playthrough.
 
I remember Torterra doing a very poor job for me--probably the worst non-yellow performance I've gotten from a starter. I don't actually remember the specifics, just that they kept doing badly. I think I may have kept running into Water-types with Ice moves but I'm not sure how common that was in DPP so I might be misremembering.
 
I remember Torterra doing a very poor job for me--probably the worst non-yellow performance I've gotten from a starter. I don't actually remember the specifics, just that they kept doing badly. I think I may have kept running into Water-types with Ice moves but I'm not sure how common that was in DPP so I might be misremembering.
I can see it actually happening. Almost everything from Unova onwards carried Stone Edge for whatever reason and kept beating my Charizard and my Butterfree.
 
I think that the closest for me would probably be Snivy. I liked its design and its evolved forms too, but I remember its move pool being so shallow and it would often have a rough time in battles as a result. Although, I don't think it had a good nature or IVs either. I didn't really regretted choosing it. I still liked raising it, I was more annoyed with Tepig becoming another Fire/Fighting starter at the time and there were a lot of cool new Fire types I wanted to try out like Volcanora and Chandelure, but Snivy wasn't quite as strong as I thought it would be. When I got B2/W2, I chose Tepig in Black 2 and Oshawott in White 2. It did help that I had a lot of fun raising an Oshawott and it's my favorite out of the fifth generation starters anyway.

I don't remember having a hard time with Rowlet in Moon and Torterra was the most solid Grass starter I chose until Rillaboom came around.
 
I remember Torterra doing a very poor job for me--probably the worst non-yellow performance I've gotten from a starter. I don't actually remember the specifics, just that they kept doing badly. I think I may have kept running into Water-types with Ice moves but I'm not sure how common that was in DPP so I might be misremembering.

I've noticed something in that regard that seems to apply to both Torterra and Empoleon: they weren't really designed for the Sinnoh region. Both struggle in very similar areas, both have rather shallow movepools with limited STAB options (for example: Empoleon only learns Metal Claw as a Steel STAB via Level Up, anything else requires a TM, which are one-shots in Gen 4), both are slow (though Rock Polish/Agility can alleviate that a bit), and there are better Grass and Water types in Sinnoh. While Empoleon suffers less than Torterra, it's only by a very little bit. Both were not really designed for Sinnoh, at least in their debut gen. Also, both tend to run into a lot of Mons that have coverage moves, like Gyarados and Floatzel running Ice Fang and various other Mons running Earthquake/Brick Break (Cynthia's Garchomp in particular runs both). So, yeah, I've noticed that Torterra and Empoleon tend to suffer a fair bit in Sinnoh, especially against various coverage moves wielding by Mons that would normally be walled by them, which Sinnoh is abundant with. In other regions they can do just fine, especially with the additions to their movepools, but in their home region they tend to have issues. Hopefully the DP remakes (if/when they come out) will help fix that issue a bit so that all three are equally viable.
 
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