Me (13 years old at the time): Dad, Mom’s cheating on you. I saw her making out with this man.
Dad: Listen here, princess. The guy’s filthy rich, and when you have money, it’s normal to have a hot mistress like your mom.
Me: But aren’t you jealous?
Dad: laughs
I was flabbergasted, lmao.


Probably not the most unhinged but a few weeks ago a coworker told me that Trump is the only president in history whose net worth went down after becoming president.
He’s not FAR right so I usually hear him out and use kid gloves to counter his arguments but I involuntarily replied, “are you out of your fucking mind?!”
Sympathies. That tightrope walk of dealing with someone who is misinformed but not malicious is tough. It’s important to challenge them, but not so stridently as to teach them not to engage with you, as you don’t want them to retreat further into that space. I wish I were more successful at it, but my mouth tends to outrun my brain. How did your colleague react to that reality check?
I actually find it quite rewarding. Not to give myself too much credit but multiple people on the right have told me I’m very easy to talk politics because I’m not outwardly judgemental when I disagree. As for this specific reality check, both of us were on our way to meetings so we shelved it. We talk politics every once in awhile and I’ve been able to change his mind on a lot of things.
Here are some tips for talking with the “soft right” (or anyone you disagree with, really):
Understand their concern before you talk about the solution, you will probably find common ground to start from.
LISTEN TO THEM. Ask questions! It’s not a lecture, you’re having a conversation.
Be smart about how you disagree. “You are wrong because of X Y Z” makes you sound like an asshole, “I’m not so sure I agree with X Y Z” shows that you’re at least considering their opinion.
You don’t know everything so be honest. “I don’t know enough to speak on it confidently” or “I can’t remember where I heard this so take it with a grain of salt…” AND if you later find out you were wrong, follow up. “Hey yesterday I told you X, it’s actually Y [link]”
If they want to back out of the conversation, let them. Maybe you’ve given them enough to think about for the day.
At the very least, be the person that makes them think, “the left isn’t all bad”