Hypothetical Hurt, Real Hurt This may be more concrete and pedestrian than you're looking for, but...
I find it difficult to draw a clean dichotomy between them, because speculative hurt is also real, not least in the way that it can lead a bitter nerd to cause realer hurt such as rape, harassment, online misogynistic trolling, etc. From this point of view it won't do to dismiss the feelings of unattractive young men who don't know how to talk to women, who feel victimized by what feels to them like an aggressively feminized culture, in which their words are policed by the online mob. Indeed, as Angela Nagle shows in Kill All Normies, the cultural dominance on the internet of political correctness and liberal call-out campaigns, which are often hysterical and puritanical, has contributed to the attractiveness of extreme misogyny and new forms of extreme right thinking, which have thrived on sites such as 4chan. I'm sure TGW could enlighten us further if he were still here.
If the speculative hurt of the misogynistic right-wing nerd is leveraged against the victims of harassment and assault, then it is useful to make that important distinction. But at the same time, if we want to understand what is happening to these young men and do something about it, we also need to take it seriously.