Earlier quoted context omitted.
> I don't think asking women on dates is automatically "inappropriate behavior". In general I agree with you but in this specific instance RMS would have been about 50 years old at the time (please see my other comment in direct response to GP). 50 year old men asking out 19 year old women is very much inappropriate behaviour.
Serious question, why is it inappropriate? It is against the "Bro Code" from "How I met your mother", but other than that? Sure, we are trained to feel uneasy about it, but if you really think about it, why exactly? Because you consider 50 year old men disgusting? Shouldn't you leave that to the women to decide? Many people also feel a bit disgusted about gay sex, yet they are supposed to tolerate and even celebrate…
Does that mean relationships with significant age gaps are wrong? No. And I didn't say that.
But do I think it's a bit off when a much older guy meets a girl young enough to be his daughter and the first thing he does is hit on her. I make no apology for that, because I'd bet nine times out of ten the girl's going to be really uncomfortable about it.