I wouldn't have an issue with lending small sums - if you're out with a friend and they were a bit short it's not a big deal to shout them $20 or so. During the lockdown a friend and I would often split four-packs of beer from our favorite brewpub and we just kept a tally of who had had what. My wife and I usually collected it because we were free during the day and every once in a while we'd settle the tally with cash. I know my friend is good for a few bucks and if he ever did let me down it would just end the arrangement.
If you're talking about the kind of money that would cause me problems if I didn't see it again, then I'd be a lot more careful.