Well no, I haven't done it yet. But this thought bothers me everyday, which means a FULL questline (aside from the Dark Brotherhood, which is pretty obvious) will get untouched as a pacifist.

I get the Tears. I tag along with Jayred. Jayred gets killed. I put the Tears in him and resurrect him with the Staff of Worms. Theoretically, his AI should make him use the Tears, thus nullifying the constant 20pt heal, thus allowing me to massacre the Gatekeeper with my Sanguine Rose.

The major question is, can I even put the Tears into the body of a dead person? Otherwise I REALLY have to use reflect damage, but that's cheating.

Any other thoughts on defeating the gatekeeper as a pacifist?