We have different approaches then. Generally, i don't prefer to meet desperate people, or people who are frustrated, with tough love.
I find it both unwarranted and unkind. That's not to say that the person doing it is unkind, but to say that its hurtful, and not in a way i find justified.
That's fine. I find coddling foolishness is hurtful and more unkind in the long run, but then again I could not be a nice person when the going gets rough. I mean, look at me! I carry a whip and I use it!
I understand your sentiment and appreciate your sincere attempt at helping him from your perspective.
I just don't think that the guy deserves to be told that he's not really nice at heart for example, just because he is for the first time (or in an early stage) meeting with some difficult things in life.
Look at it this way, if somebody mused they should rob a bank because they were desperate for money, I wouldn't allow that to be a possibility. In fact, I think that line of thinking is only making that person MORE frustrated because he or she is seriously letting go of certain ethics in order to get something, which compounds the self-loathing that's already there. If I hear any sort of musing into unethical behavior for personal gain when the person KNOWS it's unethical, I think it's important to call them out on it.
Frustrated or not, I stand by my statement that if anybody even lightly thinks about being a jerk to women, I have something to say about it, and sternly. Such statements are not to be taken lightly, IMO.