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5th Gen If the following feature existed...

I could just picture my Serperior slithering beside me. It'd make me feel more majestic, especially if I become the Pokemon Champion...
 
Off the top of my head, Zebstrika or Braviary. Those have to be some of my favorite Gen V Pokemon. Although Haxorus would also be pretty beast.
 
Only problem with Whimisicott following you is that it SHOULD blow away. If Pokémon has any logic it'd make it happen!
 
If you guys could interact with your chosen potential following Pokemon what would you want them to do? What would you imagine your potential Pokemon would do the most? Sniff trees, stare off into a distance? Would it change throughout your Unova journey??
 
I would definitely have Reshiram at the front of my party once I captured it in Black. Presumably it would have some crazy interactions when you returned to Dragonspiral Tower or the Pokémon League.

I assume Sawsbuck would be very in touch with the season in its' interactions, perhaps catching fallings leaves in its mouth (Autumn) or enjoying cold despite not being ice-type (Winter). Perhaps Electric pokémon and the likes of Klink would have different reactions in that cool cave with all the blue in (I forget the name).
 
I wouldn't normally choose Zorua or Zoroark, but if they followed you and when you interacted with then they did a little flip and turned into another Pokemon for a moment before changing back that would be a lot of fun to watch.
 
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