So here's where it gets weird/dumb: the kid replies to my friend and his parents and says, "hey mom, you put the wrong email address on my application, there's no dot in mine."
So my coworker, being the only tech savvy person on the thread replies. "Well, actually, [...]" and explains how dots are(n't) handled in Gmail address. Then the parents then reply and write, "but that's your old Gmail address, we had to get you a new one when we moved to Florida."
At this point my coworker gave up and the kid presumably lost his scholarship because his family didn't know you could keep your Gmail address when you moved houses.
(If you're reading this, hi Jake H.!)