I see what you mean. But you have to have a foundation to build off of.
Basically the person has to already be coming around to blackpill himself. He already has to be somewhat based so you can introduce the concepts slowly without him rejecting them. Then they connect the dots.
You cannot persuade bluepillers because like religious people, you'd be dismantling their strongly held belief system which they use to cope and form a worldview. It'd be like taking a sledgehammer to the head. The shock is too sudden and severe, and they perceive it as an attack. That's why they are hostile.
If they're to come around, they usually have to be burned hard through experience (like divorce rape). Often, even that doesn't work because most men cannot accept the true nature of females. Its just a waste of time, let reality sort your friend out.