Gen 1-Squirtle? Gen 2-Totodile? Gen 3-Treecko Gen 4- Turtwig I guess? Gen 5- Snivy Gen 6 -???
Based on their artwork I'd have to say Froakie.
Odd. I would've said that the "Cool Kid" would want to have a Charizard (because he thinks it is the strongest), either Feraligatr (because missing vowels are cool) or Typhlosion (same as Charizard), probably Blaziken, Infernape, and Serperior/Samurott.
For those of you starting topics about the PS4, there's a PS4 board: http://www.gamefaqs.com/boards/691087-playstation-4