Should I call her? When?

[Love'sReject]

You can't just be all soft on this kind of behavior; rapists and serial killers targeting women start out this way. One needs to ground it into his head that that behavior is not cool and it will just scare off women. Every single time, she's given clear indication that she's too scared to outright reject him but clearly doesn't want anything from him (women are like that; scared of stalkers).
Giving somebody fluffy advice that beats around the bush doesn't help anyone so I gave him the straight word.

[Wakeup]

You can't just be all soft on this kind of behavior; rapists and serial killers targeting women start out this way.

I'm wondering why you didn't use Hitler as an example? O.o

One needs to ground it into his head that that behavior is not cool and it will just scare off women.

I think we all did that already.

Every single time, she's given clear indication that she's too scared to outright reject him but clearly doesn't want anything from him (women are like that; scared of stalkers).

You've already labeled him a stalker when there is no indication that he is anything other than clueless or naive when it comes to the pursuit of women. You've also not taken into consideration that I've told him to forget women who are not putting any effort back into his own efforts.

Giving somebody fluffy advice that beats around the bush doesn't help anyone so I gave him the straight word.

I gave that to him too, silly. Then I gave him some advice on how to avoid feeling the pain of rejection so that he wouldn't feel the need to keep trying for a lost cause instead of just telling him where he went wrong.

[Love'sReject]

I think we all did that already.

It doesn't seem like YOU did; you just essentially told him what he did was OK and to blame the other girl/say it's not her loss when it's her gain that she doesn't have another stalker follow her around.

You've already labeled him a stalker when there is no indication that he is anything other than clueless or naive when it comes to the pursuit of women. You've also not taken into consideration that I've told him to forget women who are not putting any effort back into his own efforts.

Perhaps so. But I'd rather be too harsh than soft.

[Wakeup]

Perhaps so. But I'd rather be too harsh than soft.

Your perogative, love.