Yes, he did also throw himself at the Demon Ruins, beat Ceaseless Discharge, and encounter the sealed roadblock. Fortunately, Tomb of the Giants taught him to turn back at that point. Upon acquiring the Catarina Knight armor at Sen's, he's been very fond of it. On top of that, he's finally first-tried a boss since Asylum Demon, that being Iron Golem! To keep things in check, Ceaseless has beaten the Bell Gargoyles' record for the most amount of deaths he's had to a boss. Ornstein and Smough is my favorite fight in the game (as is everyone's), so I'm excited to see him reach them.

As for the new bosses:
Gaping Dragon- 1 death.
Darkroot Hydra- 2 deaths.
Chaos Witch Quelaag- 2 deaths.
Ceaseless Discharge- 21 deaths.
Iron Golem- 0 deaths, first-tried.