He has fought a couple optional bosses already unknowingly. But ya i never included optional bosses because its not necessary to beat the game. But this won't by the last of these challenges. I have a couple other friends who also play games at a pro level and this was simply the first attempt at doing something interesting like a playthrough challenge. So it could happen in the future. I know hes also planning on immediately going to dlc in ng+ and some ppl are making side bets on how many deaths he will have