Jack has to survive this gauntlet of DOOOOM! How many does he make it through?
R1: 1000 Papercuts on the most vulnerable parts of his body
R2: Resist the urge to become a meme and to act like a completely normal character that's not meme-able.
R3: Resist seduction from girls that would normally only exist in his wildest fantasies.
R4: Play Dark Souls on maximum difficulty for the rest of his life and die a natural death. It is assumed he is locked in an indestructible room, and he has no need for nutrition or water. Can he do it without suiciding!?
Literally doesn't even have to use flesh manipulation, not sure paper can even cut him.
BEGONE T H O T (Then again, his wildest fantasies involve flat is justice and a girl who actually likes him for more then reproductive capacities, so, the idea that they would be seducing him is probably just either going to be a normal slightly flirty conversation or a paradox that kills everyone)
So he's going to be playing it probably for like 120 years considering Longevity, and considering his patience and capacity to "git gud", he probably has time to end up searching every nook and cranny and do a total no hit run of the entire franchise.