It's a fair discussion to have, and in fact such dialogues should be had by all factions of all parties on basically a continuous basis. Ideally, that's how you arrive at improvement.
But I wouldn't expend to much energy in trying to win the deplorables over. Take a look at the folks who attended the pro-Clownstick "rally" (there were apparently somewhere between ten and fifty people there, so....) in Jefferson City,
I mean, think about it. These are obviously people who eke their way through life on a pittance, and here they are voluntarily showing their heartfelt support for a spoiled hectomillionaire who's in hock to the Russian mob and using the office as a profit center for his deals with the Chinese, who wouldn't piss on their heads if they were on fire. Clownstick doesn't give two shits about them, or anyone else besides himself. If they've paid any attention at all to his life history before the scampaign infomercial-rally bullshit, they know this already, whether they admit it or not.
This doesn't mean completely write them off, but it also doesn't mean the Dems should expend too much effort chasing after them. The phrase "come correct" comes to mind, that if Dems approach these folks with respect and understanding, they might get an audience. But it might also be political version of Winter's Bone, where people are the way they are, because that's how they've always been, and they're not interested in learning or changing much of anything.
Despite the innate skepticism many on the left have about the "economic anxiety" bloc, many of the Clownstickers are economically anxious, and in any case, what they really want is to see and hear that more attention is being paid to those issues than to transgendered bathroom use or whatever social justice cause is making the rounds.
This is not to minimize those things at all, but it is a call to look at the aggregate numbers realistically and play the odds accordingly. And the real numbers are in motivating non-voters to get out and vote, but it wouldn't hurt to at least cast a glance in the direction of the deplorables and see if they'll at least listen for two seconds. But it's an uphill struggle convincing low-info voters. Obviously they care very little about empirical facts as much as they need to feel that you will walk your talk.
I sincerely believe that if an agenda of economic justice for all is pursued, the social justice issues will fall into place much more easily. People who have a little more discretionary income and hope for the future do not have time to fixate on who's using which bathroom. And the Democrats are in a fine position to test that theory.