two contrasting views on (among other things) lifestyles

Let's start at 3:05 in this Russell Brand video (embedded earlier) and go to about 4:06:

That sure sounds a lot like libertarianism, or something close to it: you do you, and let me do me. Don't tell me how to live my life, and I won't tell you how to live yours. In this framework, tolerance is an essential value. Now, let's look at this Matt Walsh video, starting at about 3:55:

Walsh is framing his argument from the perspective of objective reality, and his viewpoint, while honest, is certainly much less tolerant, and here we can see a crucial difference between a (presumably) libertarian point of view and a more decidedly conservative point of view. Walsh is saying the subjective can never trump the objective: incorrect usage of pronouns, etc., is a form of lying, and people deserve the truth. A person with a Y chromosome is objectively male; a person without a Y chromosome is objectively female.

I see and actually accept many of Walsh's points, but I think I sympathize more with Brand's seeming libertarianism than with Walsh's starker, less tolerant take. I've previously said that I have no trouble, for example, referring to a drag queen as "she." I know the drag queen is biologically male, but I'm willing to make the allowance that this person, for whatever reason, identifies as female. Walsh rejects the sex/gender dichotomy because he sees it as delusional; I see the dichotomy as a road to tolerant coexistence, and while I'd concede that the objective trumps the subjective, there has to remain room for the subjective: that's where individuality lies. The subjective has weight; it matters. What do I care, after all, about what's happening inside your head, and what business is it of mine? As long as you're not hurting or oppressing anyone else, I have no reason to care what you do or how you think. This is, overall, more in line with what Russell Brand is saying than with what Matt Walsh is saying.

I find Matt Walsh useful to listen to because, as I'm discovering through his videos, he tends to be a pretty clear thinker. But he's also a strictly doctrinaire thinker, which makes me view him and his intolerance (for lack of a better word) with caution. I've seen enough of his videos to know he doesn't actively wish harm upon the trans community, but he often comes dangerously close to accusing that community of being a gang of liars and insane people. I appreciate the aggressive caution he brings to the issue of "grooming" children; in such instances, I find I'm thoroughly on Walsh's side. Little kids are far too young to know what they want; in the above speech, Walsh notes that his own kid couldn't decide what he wanted at a restaurant, so how on earth can a kid that age make major decisions about his sexual future? I think Walsh also points out, later on during a Q&A session, that the whole "trans" thing is much more a problem in richer societies than in poorer ones: poor people from desperately poor countries can't even understand or relate to "trans" issues.

That said, I think Russell Brand's notion of peaceful coexistence in a libertarian spirit is more where I'm at. I don't want to live my life angry and cautious and tribal all the time, always on the alert for a new thing to be offended by. That, ironically, is what so many on the left are doing these days. I'd rather live among people who can take a joke, who don't mind occasionally ribbing and offending each other, yet who see it as a genuine plus to be exposed to different perspectives and ways of living. Exposure to difference gives us all a chance to learn and grow. On the other hand: what is the cut-off age for when it's appropriate to talk to kids about "trans" issues? I don't know. I personally think kids do need to gain some understanding of today's sexually polymorphic reality, but teach them about it below third grade? No. Absolutely not. 

I'm trying to express a nuanced view, here; I don't think the world is as black and white as Walsh makes it out to be, but at the same time, it should be obvious that there are some limits to acceptable discourse. Tolerance is necessary, but it's not infinite. It can't be.