Is that a Templesmith?
Hell yeah it is. <3
Funny story! I played my Pokemon Y game as Stiles and my main was a Houndoom named Derek, no lie. But that was just me trying to be funny.
In all honesty though, I feel like Derek would be a Dark or Steel type trainer, so maybe he’d be the one who’d use a Houndoom. I can picture him with a Skarmory too? Maybe an Absol, too.
Stiles is way harder for me to pin down. I’m torn between feeling like he’d be pretty earth-y, or he’d be straight up psychic/ghost. Down that avenue, I think he’d work really well with a Gengar, maybe a Swoobat or a Reuniclus? If he were more earth-y oriented, I think he’d work well with a Sudowoodo, maybe a Breloom?
This might be the most difficult headcanon question anyone’s ever asked me. I’m going to have to think about this one more.