What weapon are you using? If you use weapons with long reach like Hunter Axe or Ludwig Holy Blade, the bosses will be more manageable.
I'm now playing the lower Chalice dungeons and some of the bosses are harder than in the main game. Like I faced Blood Starved Beast again in Ailing Loran Chalice but this time he is tougher and you fight him in open space, no wall to hide behind. I a bit scared to go to the Defiled Chalice that halves your hp.
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