> The problem is, I don't believe a single one of my male friends (or female friends) would be capable of doing something like this.
I know guys who I wouldn't be surprised to see do something like this, mostly from the bar I go to. I have female friends who know lots of guys who would stoop to this. They would not necessarily believe there's a lot wrong with it, and might welcome the advance if they liked the way he looked or acted. This guy did it sight unseen though, I can't see any of my friends going for that.
There's a pervasive element in society of success in dating requiring playing a numbers game, on both sides of the gender fence. My female friends all expect me to be asking out any girl I think is attractive. Being asked out is something that just happens all the time for them, they just seem to get used to it. The context matters mostly as a signal for what it's going to be like to date them.
An attractive female coworker of mine told me about how a lawyer who hires her on the side to help him with document stuff asked her to dinner on a business pretext and at that dinner was feeling her out for willingness to date him. I was surprised that she accepted his invitation and didn't slam him for being a creep for his behavior. She thought it was weird but didn't have a huge reaction or anything, she told me like one might talk about any weird thing that happens to you in the course of a day.
I have one IRL female friend who was a feminist and would definitely see something wrong with this behavior. She's also extremely attractive and describes getting hit on constantly. She definitely does not have a neutral reaction to it. But she also relayed her fear to me that she'll never be able to get married because feminism.