My my concern about that is that if he is doing that with a lot of other Users it smells phishy at some way.
Just a few Reports is enough for a temporary ban
Reporting it will be a harsh move, why would I do that to get someone punished for a very little unsensual activity however it will surprise me if anyone ask me for even a $1 and if I did not have any interaction with them before - at-least some memory of interacting with them before is okay for me. If I was suspicious I would do the same as Lafu did.