Me and my close friend would send each other crypto when owning up for stuff like paying the rest of the half of the food
Same, I almost convinced a friend of mine to start settling debts in crypto, but he later decided not to because he had heard that this could be a "taxable event" and wanted to be squarely obedient to the IRS.
Now lately it just carries this dark atmosphere of being used for bad and illegal services.
I explained how Monero could fix that, but he immediately said no because he had heard about "bad actors" using Monero. He wanted to use algorand. Some people don't want to be saved.
The other issue I've encountered is that the moment I mention crypto, people are immediately thinking "How does this scam work?"
Just recently I was trying to sell something on Facebook Marketplace and the guy wanted me to deliver. I agreed but I was going to use Uber Courier to deliver and thus I'd require payment up front. I told him he could pay with Zelle, but he said he didn't have any of that. So I offered him the option to deposit cash into his local Bitcoin ATM to send to me. I told him I understand if he wouldn't want to since this is exactly how some scams on there work since there's no guarantee I'd even send the thing to him. He never replied.
The price of anonymity with XMR is trust.