How do you actually engage and assess views that oppose your own?

[Wild at Heart]

I don't generally debate something unless I truly believe I:

1. Know the facts extremely well and have something to say about the topic.
2. Feel like my rights or identity are being infringed on, and debating is pushing back against tyranny or bullying​

This has changed with age, I was a debating little prick when I was younger. I now realize I don't care what other people think, and everyone is so extreme these days that debates never get us anywhere. You can be true to yourself and not engage in meaningless debates because someone said your favorite video game sucks.

If I was presented with a meaningful debate, and I was given opposing viewpoints, I usually examine the validity and track record of the opponent. Are they often one who bows to groupthink, or an over reliance on data from tainted mediums (the news and social media) ? Do they respect my input, are they even reading my points, or are they just glazing over them to say their next gotcha moment? Can they even comprehend what I'm saying? I've had hours long debates where I finally realized the person couldn't understand the simple concepts I was laying out, so I gave up. I'm going to be honest, as a man, I find most debatebros to be beta males who want to intellectually pull down the pants of assertive men and try to show dominance. This is why they cling to debate concepts and bark out things like "slippery slope!" when you make a point. They know you don't understand half these terms, and haven't prepared a dossier of sources like they have for their life-changing ambush on you that will help them climb socially after dunking on you.

In a meaningful debate with an equal who respects my view and isn't just parroting talking points (this has never happened in my many years) I would try to work towards common ground. Any debate I find meaningful would usually be over ethics or philosophy, in which a compromise is the moral outcome (when dealing with a sane person). When I've had debates that go into #2 on my list, they were usually me fighting back to actually argue for equality when someone was reaching over the line and messing with me and my rights.

Sorry for the cop-out answer, but i find debates to be useless in most settings. Society has changed and we aren't Greeks in the Senate anymore. People change their views after watching a youtube video or reading a social media post (an individual debating the air.) I take the time to seek out and research things, and form opinions after ruminating. Therefore I detest people who make snap judgements, or have kneejerk debate reactions after hearing about a concept for the first time. Therefore I haven't had my opinion changed on many things, as I see the thought leaders and debatebros of the day suck their opinion through a straw and swallow it without thinking.

 

[John Titor]

The first thing to assess is if the purpose of the conversation is worth pursuing in the first place. So for example, you may want to have a conversation with someone because you're open to changing your ideas and want new information, or you want to see opposing views and explore them so that you can refute them better later on, maybe it's just to try to make a fool out of someone, or maybe it's to change their ideas (likely you won't).

However it may not be worth pursuing if the other person is extremely close-minded, or is being a retard, if it's devolving into a slap fight, if the other person literally does not understand what you're saying, etc.

It depends on a case by case basis, but "generally" on the Internet it's a waste of time (specially if on Twitter or Reddit from my experience, Twitter is not even designed to have deep conversations anyways).

Maybe the best place you can go to challenge your and others ideas is something like a public Discord server that is centered around philosophy for example. I've been in a couple, slap fights were discouraged by the rules, there was coverage of a lot of topics (including transgenderism since you mention that), and regulars there at least tried to make proper arguments instead of stuff you see on Xitter.

You're still going to get people ultra-sensitive when in regards to "gender/trans" topics, and unreasonable pedantic assholes that think too high of themselves because they have a degree in philosophy.

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I'd say in general approach topics with skepticism and be honest with yourself. That means that you should identify if you have bias towards some conclusion and why, and if truth matters less than what you want it to be.

But everything can be questioned and things don't have to be black or white, so get acquainted with logical reasoning and fallacies, so that your questioning can have solid grounds.

I feel this. I can be civil with people I'm friendly with or have shown me some form of courtesy and avoid the types who would stomp their feet and scream when things don't go their way because I know nothing productive will come out of it. I knew someone who thinks shouting until the other side gives up is a legitimate debate tactic, that's the kind of people you should not bother with.

 

[Otterly]

I read stuff from all over. When I have an instant reaction to it, I stop and think again. Why am I reacting? Are there merits to this argument? How is it trying to make me feel? Does it present genuine evidence to say I’m right or wrong in my reaction?
Since Coof in particular I’ve tried very hard to actually look a bit more at evidence presented for ‘settled’ concepts. I no longer dismiss anything out of hand. I accept I have certain opinions, and open to having some of them changed. Others I find absolute, but all of those are moral boundaries rather than ‘factual’ ones. Nobody will be convincing me that up to birth abortion for no reason is fine, nor that trooning out kids is Ok.
If it’s a factual opinion, I’ll look at it. I’ve enjoyed looking at @High-Fructose Corn Syrup s posts as a good example. My reaction to HFCS is ‘shit is bad’ but he (I’m assuming you’re male) has presented evidence it’s no worse than sugar. Next time I see an article or paper on it I’ll look at that as well, and I’ll take both sides, combine it with my own knowledge and make a choice.

I think there’s another point here which is that you do need some kind of anchor point in life that’s an absolute, and if you have none and thinks everything’s a social construct you’re in great danger of nihilism and being open to social engineering. Having absolute MORAL thoughts is fine.

 

[Mnutu]

Ask first if the opinion stated is based or cringe.
If it is cringe, post Soyjak.jpg and call the poster a fag.
If it is based, post Chad.png and pretend like I’ve always held the opinion.

When another opinion arrives that contradicts the prior based opinion, and it is determined to be more based, DFE and start over.