I have three characters in mind right away, Arianne (Trainers), Charlotte Grace (Together Forever) and Hikaru (Hoenn Square 1) because... yeah, I probably made them rather similar on the surface. They're all outgoing, reckless to a certain degree, coming from similar backgrounds, and of course they're all Pokémon trainers... kind of. Putting them together would be very interesting, though, because there could be many nuances and differences that could emerge! Out of the three, Arianne is the only one who is supposed to be truly reckless and not stop at anything, whereas Hikaru and especially Charlotte would eventually get scared and regret their own choices. Arianne is also the only one who I've tried to give more development and backstory, as opposed to the other two. All of them have some nuance to the way they approach new people, too, and in fact that's the only situation where Arianne is supposed to be less reckless and more of a people pleaser, always hoping that people have a good opinion of her - the opposite of Hikaru in that sense!