Personally, my redpilling story started in 2015 when news were being reported about gang raping of European women by Muslim immigrants. Those stories prompted me to vote for Trump (since he talked about being hard on immigration). I didn’t expect him to win, but I was pleasantly surprised when he did. As time passed, the propaganda machine that is the mainstream media became increasingly more evident. Dave Rubin, Jordan Peterson, Steven Crowder, Ben Shapiro (before he revealed himself to be a complete traitor), etc., were all people that helped me understand how evil and power hungry the Democratic Party is.
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Fake news gunna fake news. But there might be a time when they're telling something truthful where you can make a comment that'll let him know you're on the same side. Just don't interject when you know it's BS until he's open to hear what you have to say.