I despise these challenges as they're just insulting and cruel most of the time. It's one thing if a kid does it back and forth with their parents and enjoys being teases (I saw that one boy in the middle who laughed at his Dad doing it), but for those who don't like that or who actually have trust problems because of it, it's just a really not nice thing to do that isn't the best idea.
Heck, one of my biggest causes for trust issues is due to how many of my GBA/GB/GCN games were flat out stolen by my birth mother and pawned for money to use on products not right in a home with a child in it, and whenever I wondered where a favorite game went, she'd make a stupid excuse like "you must have lost it" or something.
I believed her until I learned through my grandparents and my own mom that she did pawn a ton of stuff and thus I lost lots of great games for no reason. (I also learned that she tried pawning my prized copy of Pokemon Emerald once, my favorite GBA game, and I apparently DID figure this out to the point I nearly destroyed the apartment room in anger, but thankfully she got it back...) Smash Melee, Double Dash, Hamtaro Ham Ham Heartbreak, Mario Advances 1 and 4... And many others. I still haven't gotten back a copy of Double Dash, SSBM or Hamtaro to this day due to newer games being out and second hand copies being so expensive. D: I'm just glad I never had Cubivore or Path of Radiance growing up. So yeah, while I doubt any of these parents are like my birth mom, actions like these can cause trust issues in kids if they aren't told ahead of time or if the kid doesn't know their parents are teasing goofs.
...Speaking of which, I still remember being the guy who used to tease his best friend by ejecting his 3DS Cart in the middle of a game. (Kid Icarus Uprising) I don't know why I did it but we practically took turns doing it and it was all in silly fun, which is why I'm hit or miss on these challenges. It's not as outright cruel as the Candy one, but it's still something I think that I don't think Jimmy should egg on.