He had never cried, and he couldn't understand why almost every failure brought Obito to tears. For him a failure was a cause to try harder, not an excuse to give up and cry for someone stronger to help. There was no one stronger here, you had to help yourself.
He had never cried, but Obito had sensitive eyes that couldn't cope with the dust and dirt and pollen. Kakashi had bought him the garish goggles to see if that would stop him from crying, but there was still the tell-tale dampness on his cheeks.
He had never cried, because his father had cried - knelt there with his wakizashi in his hands, begging for his forgiveness; begging Kakashi, begging Konoha, begging anyone that would listen. There had been no one but Kakashi.
He had never cried, but Obito did, and Rin knew - as the left side of his mask darkened across his cheek - that is wasn't Kakashi crying. Kakashi never cried. Instead, Obito would cry for him.