When arguing with a moderate liberal (one who isn't becoming emotionally violent when having a discussion) and the goal is to red-pill them, I believe we need to stop taking an offensive position in order to convince them of anything. The liberal argument is strongest on the attack position since they charge w/ emotion, and weakest on the defense position since nothing they believe actually makes any sense.

The answer I believe is to ONLY ask questions, bring up their side's contradictions whenever possible, and never go on the offensive.

This automatically forces them to defend. This works three ways. The first is that it forces them to think about the WHY instead of just regurgitating their talking points to you. The second is that when you inevitably bring up a contradictory view of theirs, they will be forced on the spot to make it make sense, which, of course, they won't be able to do. The third is that they won't be able to spout their cookie-cutter talking points that they are fed by MSM, and actually attempt to use reason.

Example: "Trump is racist and sexist and homophobic." - What has he said or done to make you think that? Why is is okay for Hillary Clinton to call black people super predators? Why is it okay to have a former KKK grand wizard as a mentor? Why does Trump have women, minorities, and gays throughout his administration? etc.

Obviously it'll be easier when they give you a specific point to address, but the key is to ALWAYS, no matter what, keep them defending their side.

This isn't ground-breaking stuff. WE all know these arguments, but the purpose is to simply break the illusion that grasps these people, and force them to think, rather than feel. As Breitbart said, the dirtiest trick you can play on a leftist is to play their own words back to them. Let me know how it goes.