I was once very poor and now pretty well-off. I’m generally happy to try and pick up the bill when I go out with friends and family because I’m thankfully in a place in my life I can do that and I remember how thankful I was for the generosity of others early in my life. Unfortunately I’ve found some people get offended… that my picking up the bill is some power move to show I’m rich so I’ve become reluctant to do that unless I’ve explicitly invited them to dinner or whatever. I don’t want people to think I’m showing off and trying to make them feel inferior so if they’ve invited me or it’s an otherwise group event, I assume they’re paying their own way and didn’t come with the idea that someone else was paying for them. If somehow I’m the one whose credit card it ends up on because the place won’t split the bill, I’ll let people know how to Venmo me or whatever. It’s not because I’m worried about the money though.