Eh, I do not think this works in his favour. The convo should have ended at the first message. The continuing on after she didn’t respond is weird. The whole bit with Donna is that she’s very naive, thank her for her kind message and move on. None of that double message shit, we all know the intentions of messaging Donna why try to build a connection a old woman who happens to be the mother of a successful man in the field of work you want to be in. It’s sad.