I'm going to repeat, once again, there are a number of very compelling reasons that you shouldn't "debate" right wingers.

Ben Shapiro and Kaitlin Bennet are not going to be convinced to drop their extremely lucrative hate careers because you zinged them in a talking contest.
The most important reason not to debate right wingers is because the things we're called upon to debate with them

SHOULD.
NOT.
BE.
DEBATED.

Black people have a right not to be murdered by cops. Trans women are women, trans men are men, enbies exist. These aren't negotiable.
If I come to the debate with "cops shouldn't have the power to summarily end someone's life without trial" and that's something they seriously want to argue about?

No.

That's my answer. No. You don't get to debate that. That's not up for discussion.
Allowing things to be argued that should not be argued INCREASES THE PUBLIC PERCEPTION THAT THESE ARE THINGS THAT CAN OR SHOULD BE ARGUED OVER.

If you allow a debate to occur over fundamental human rights, they stop looking fundamental and start looking negotiable.
Second reason: debate is not a magic spell.

Debate only works if both parties enter it with honesty and full intention to change their viewpoint if the other side presents a more compelling and well-reasoned argument.

DEBATE CANNOT MAGICALLY ENSURE THESE CONDITIONS.
You can make the most eloquent, fact-checked, well-reasoned argument for trans rights, and your opponent can still just refuse to be swayed by it - and that refusal is indistinguishable from your argument being insufficient.

It's impossible to PROVE they're acting in bad faith.
Thirdly, it places the responsibility of oppression upon the oppressed for not being better debaters.

Do these people really think that if Jews had had better debate skills, the Holocaust wouldn't have happened? That indigenous people could have convinced colonisers to leave?
It places the responsibility for the oppression that marginalised people PROVABLY EXPERIENCE upon themselves for not being better at convincing the people doing it to stop.

I'd say that this is clearly ridiculous, but the fact I have to write this thread suggests otherwise.
Fourthly, and this is the most applicable to Ben Shapiro: IDEOLOGY COMES FROM THE MATERIAL CONDITIONS WE OCCUPY.

It takes immense effort to convince someone to take on an ideology that doesn't materially benefit them.
Ben Shapiro, Kaitlin Bennet, Steven Crowder, etc. - they make a lot of money and have a lot of fans because they convince people who already believe that conservative capitalist ideology is correct that they're right.

They have a material incentive not to change their mind.
Do you think Steven Crowder, the man who only makes any money at all because he appeals to a weird crowd of right-wing whineboys on YouTube, is going to suddenly give that all up because you arranged a few words in the correct order? Your rhetorical skills are THAT good?
Ben Shapiro's material conditions will never be negatively affected because he loses a debate. Like, if being publicly wrong affected Ben Shapiro's ability to make money in any way, 20 seconds of @hbomberguy destroying his own set and screaming would've ended Ben's career.
I think I'm pretty good at debating, but I am not arrogant enough to imagine that I have the power to debate Ben Shapiro into giving up his 2.4 million followers and however many thousands he makes per month spewing right-wing propaganda.

I'm not THAT good.
Maybe you could convince me that Inu Yasha is a good anime, because my belief that Inu Yasha is boring and mediocre does not really affect my ability to live happily.

You cannot convince me that conservatism best serves my personal interests, because I KNOW IT DOESN'T.
Finally: right-wingers wouldn't tell you to debate them if it actually worked.

This is mostly @CaseyExplosion's observation, but it bears repeating: people telling you "you can run, but you can't hide" probably aren't incentivised to tell you that hiding actually works.
Why would right-wingers - who obviously believe that their worldview is already correct - just GIVE you an effective means to combat that worldview?

This ain't Dragonball Z. They ain't Goku. They're not handing you the advantage so that they can have a fair fight with you.
If there was an easy, straightforward way to ruin the ideology that allows billionaires to fund Ben Shapiro or Steven Crowder's wealthy, comfortable lifestyles, they would not simply tell you what it was.

They're many things, but they're not stupid. They play stupid on TV.
To sum up:

1. Some ideas are non-negotiable.
2. Debate doesn't compel people to change their mind.
3. You shouldn't have to convince people not to mistreat you.
4. Right-wingers are invested in never changing their mind.
5. Right-wingers wouldn't tell you how to defeat them.
You can follow @vexwerewolf.
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