Considering the general sense of humor displayed thus far, I don't think that's too critical an issue. Or rather, given the format (lob suggestions and roll out) goofiness was an anticipated and expected occurrence
If I had to guess, befriending him might have worked for a while, and then just when he's feeling better, depression rears it's ugly head and he thinks "No, he's just like all the others. He'll leave, and die and die and die and then finally turn and I can't..." and the Despair/Prayer occurs and the boss fight is on once more.
If I had to guess, befriending him might have worked for a while, and then just when he's feeling better, depression rears it's ugly head and he thinks "No, he's just like all the others. He'll leave, and die and die and die and then finally turn and I can't..." and the Despair/Prayer occurs and the boss fight is on once more.