Even the ugliest fat bastard from /vp/ would be "kinda cute" in some way after passing the pokemon treatment. Also remember that age of consent is not a thing there, you can pretty much date every trainer older than 10. Let's suppose you are somehow inserted into the pokeworld, keeping your current age and looks. Who would you go after, and what are your chances with her?
I'm not sure if 14 yo Gloria is into average looking 26 yo guys, but i would try anyway.