[wrmanis]

In my case it's an issue of relative income - I have a large group of friends that have been together for more than a decade and our income levels have dramatically diverged. We're very comfortable with each other but there's an undercurrent of social implication whenever we go out to somewhere on the nicer side, or somewhere that's a little out of their normal routine.

Like several other commenters in this thread, I have more than I need and really enjoy spending time with my friends, so I naturally pick up the bill whenever I can. My friends are appreciative, but they also feel awkward about going out with me sometimes because it feels like they're implicitly asking me to pay, which in their minds is unfair and uncouth. It also could be interpreted as me suggesting that they couldn't pay for themselves.

Another layer of this is that most of my friends were raised in Asian cultures, where fighting over the bill is normal and even expected. It's hard to fight for a $500 restaurant bill for 10 people on near minimum wage, so you can imagine some real mixed emotions when the server obviously doesn't want to split it. I'll pick it up every time, but it's naturally a hit to your pride when compounded over the years no matter how gracious you are about it.

Like the OP of the article, I spend a lot of time thinking about the dynamics at play here. I love and respect my friends, but frankly a weekend at an AirBnB the beach or even a modest ski vacation is just out of their price range most of the time. Sometimes it really is easier if you phrase it with a little white lie about how it came to be in order to preserve their pride, because the real important thing is getting to spend time together.