No, that's not quite enough despair.
Shirou declaring that he would damn himself to an eternal hell with a smile on his face if it meant he would save his friends? That would do it.
Cue Nanoha and Fate realizing that their chosen professions will give Shirou plenty of reasons to needlessly endanger his life and afterlife for their sake.
EDIT: Naturally, he smiles reassuringly the entire time.