I'd say that the time he was in the most danger, even though it was easy to play, was the babysitter. He didn't know much about walkers, and it caught him off guard and without a weapon. Even more threatening is the fact that the thing is actually very close to biting him as he doesn't know how to handle fighting it off of himself. The only reason he survived at all was the convenient weapon given to him.
I have Anatidaephobia