The Rockiest Start.

[Palamon]

Of all our main characters that started their Pokemon Journey in the anime, which one do you feel had the roughest/rockiest start? Which one do you feel had the easiest transition into being a Pokemon Trainer?

 

[Horn]

Roughest? Definitely Ash. Even though May never even wanted to be a trainer, and one may consider that a rough start, IMO she still had it easier than Ash. Seriously, oversleeping thanks to broken clock, being ridiculed by your rival in front of his (and probably your) friends, scolded by Professor Oak, getting Pokémon, who doesn't like you, standing in pyjamas in front of most of your mother's friends, being hit by pack of enraged Spearow and being joined by bitchy girl, who only joined you because your Pokémon scorched her bike in attempt to save you? What ever can beat this as worst start of Pokémon Journey?

Easiest? I am tempted to say Trip, but he most likely will not count as main character. In all seriousness, though, Dawn. She knew all rookie needs to know about training Pokémon, she already had her goal and she was joined soon by two friendly and experienced trainers. Yes, she had it quite easy.

 

[FireSnow]

^ Honestly, couldn't have said it any better myself. Ash had easily the worst start to being a Trainer in the history of Pokemon. I'd be thoroughly amazed if anyone else could beat that. And Dawn was barely a rookie it felt like since she actually knew what she was supposed, in contrast to Ash, May, and even Iris to a degree and then getting a Gym Leader and a veteran of three different regions to help guide you a bit is pretty helpful I'd say

Special shout out to May though for flat out being scared of Pokemon at her beginning. Not what what you typically look for in a potential trainer considering a love for, or at least not scared of, Pokemon is kinda important I'd say.

 

[AliceBlaze]

I agree that Ash had the roughest start.

As well as Dawn, I think Serena had it easy as well. She safely and easily travels from Vaniville Town to Lumiose City with no Pokemon on hand, makes a good first impression with Fennekin and apart from nearly being attacked by a Vespiquen, she seemed able to take care of herself even before meeting up with Ash.