You're a Cute Nerd

First person to guess who these characters are, what series they're from, what episode and season/saga they're from gets a free commission! Whatever you want!
People who guess after...you will receive a cookie. '-'

I just really like this pairing. I'm surprised nobody shipped it. I mean, it may be a bit of a one time thing and the fandom isn't that huge as far as I'm aware, but still...How could one miss it? Hot cool guy and cute nerdy boy? Seriously, we need to expand on characters here. >w>;