How does her hat stay on?

I would guess the pic itself is photoshop. Human snowboarding is kind of "real" in that it's happened but isn't exactly a sport.
https://www.instagram.com/p/BffEA-aA1mO/
FYI ^ those people want this called the "snurferdawgchallenge" apparently, which implies at least one of them thinks it would be a good idea for other people to try. The chiropractors of the world were likely running low on patients anyway I guess.
As for what happens to the guy? This hill actually slides directly into an off-screen sex-dungeon, where he is often heard from, but never seen again.