The one problem I see with most people discussing things with "the other side" is that they don't genuinely care, nor would be ever swayed by what the other person says. It's just a game of "gotcha" most of the time and thus unproductive.
Some people are so anti-Republican or anti-Democrat that you might as well be trying to convince a Jihadi to eat bacon or a Catholic to abort a pregnancy or a Baptist to star in gay porn -- or a Mormon to play blackjack -- or an Atheist to become a Buddhist monk. Online forums (and newspaper comment sections) have created such a political balkanization as to make participating nothing more than sadomasochistic entertainment.
I used to care about those sorts of discussions with the "other side," but I've found that the level of discourse has devolved into to some variation of "Trump wants to send people to the gas chambers and destroy the planet" or "Hillary hires hitmen and Bill took a payoff from the Russians." Or, often it's "America is horrible and should be boycotted" -- or some other hyperbolic rant based on an anecdotal news item about a brown person at an airport.
I've got no use for it. I vote, encourage my like minded friends to vote and that's about it. Occasionally, I'll get sucked into a political discussion on Hacker News, but pretty much instantly regret it. I'm ok with the "crowd" disagreeing with my politics -- but I definitely don't relish getting into intense political debates with people here that I'd probably like to call my friends in real life.
Maybe it's my age (I just turned 40,) but I feel like engaging with deep economics and political discussions with those under 25 to be bordering on pointless. There are exceptions obviously, but when a 19 year old college sophomore wants to tell me about business unit economics, tax policy or building permits -- I'm pretty closed minded simply because they're generally citing other people's ideas rather than ideas based on actual experience or original thought grounded in experience. But that's ok. Views change as we begin to see the world for what it is rather than as what we want it to be. Everyone has the right to be wrong -- even me, as rare as that is. ;)
I'll leave you with a quote that is attributed to many people but this version came from Anselme Batbie, a 19th century French politician..
Celui qui n’est pas républicain à vingt ans fait douter de la générosité de son âme; mais celui qui, après trente ans, persévère, fait douter de la rectitude de son esprit.