Suppose a self-appointed Conservative "leader" consistently labeled homosexual activity, and the whole subculture as wrong, but always with a "wink, wink; nudge, nudge; say no more" attitude that reassures his readers that he is not one of those nasty people who actually believe it is really wrong, but that he is obliged by his position to sorta kinda condemn it a little. Suppose that this same "leader" has been unsparing in his criticism of Trump, but would have us believe that Biden is a well-meaning old man who could not be blamed for the actions his administration and party would likely take were he to be elected, to say nothing of his record in office over the past several decades. Likewise, this "Conservative leader" wants us to know what a fine, praiseworthy woman Ruth Bader Ginsburg was, consequences for the unborn be damned.
You might then reasonably conclude that the word "Conservative" did not mean much to this person, except perhaps a meal ticket.
Now step back and consider: although I have one particular person in mind, you could really put the names of all the prominent "Conservatives" over the past three decades into a hat, draw one name at random, and there is a good chance the description above applies to the owner of that name, too.
Seven years ago I said that I could not call myself a Conservative because that label carries too many connotations. That remains true. It is interesting, though, that the same label also carries too little meaning.
If you could live out one of these alter egos for two weeks, experiencing the world through their eyes, which do you think would bring you the most useful new understanding of the world:
the opposite sex
a different race
someone from a non-WEIRD (Western, Educated, Industrialized, Rich, Democratic) country [or, for my readers who live in a non-WEIRD country, a WEIRD one]?
This post illustrates an error that is disturbingly common today, even among people who should know better: the error that our bodies are superficial "shells" that are as external to our being and as interchangeable as clothes. This is not the Christian teaching, which is that the body is on integral part of any human being -- which is why we do not become angels after we die, we await (hopefully in Heaven!) the General Resurrection which will reunite our souls with our bodies. This also is also important to understand the Incarnation and the Resurrection of Jesus: He did not take on human nature for a mere thirty-something years, but forevermore. No, this is the sort of thing one would expect from a Gnostic, a Buddhist, or a Hindu.
We can imagine being all manner of things that we are not and cannot become, like a different race or sex, as Dreher suggests; but we cannot actually become those other things, and therefore we cannot genuinely see things from their perspectives. It is not enough to experience the same circumstances. A person's perspective also comes from his or her strengths and weaknesses, his or her world view and philosophical framework, his or her body of previous experiences, and it is not ultimately possible to share all these without actually being that other person; but we cannot be that person without ceasing to be ourselves.
Meanwhile, it is dangerous to treat our imaginations as though they were actual data. Seriously, think back to how you imagined some major change in your life would be -- going off to college, a developing romance, a move to a new city, a new job, etc. Now think how different the actual experiences were from what you had imagined. If you have such difficulty imagining yourself in slightly different circumstances, how much should you trust your imagination of being a different person?
Sadly, this is par for the course with Dreher and The American Conservative.
EDIT: A valid objection would be that all Dreher is asking for is imagination, and one of the purposes of imagination is to consider what we cannot directly experience. For example, we can start with the assumption that there is a largest prime number and show that that assumption leads to a contradiction. It is hard to see how such reasoning could be applied to a man imagining he is a woman, though; contradiction would only tell him that he is not a woman, which he hopefully already knew. In fact, it is only the reasoning after the assumption of a largest prime number that makes the assumption useful. Dreher's suggestion, though, is really imagination for the sake of imagination, not imagination for the sake of reason. In the middle of Weirdmageddon, when most of the world is trapped in Mabel's wish-fulfillment prison, what we really need is more reason, not more imagination.
EDIT 2: I mean, come on! This is clearly Portland in 2020.