It's not that black and white, is it? Maybe thousands of dollars is a bit much (unless you're quite wealthy), but I've certainly helped pay for plane tickets, h

It's not that black and white, is it? Maybe thousands of dollars is a bit much (unless you're quite wealthy), but I've certainly helped pay for plane tickets, hotels, concert tickets, etc. for my friends (usually ranging from like $50-$300 though, not thousands). It's not like "Hey, I'm rich and I'm just going to buy out the entire concert so we can have a private show", more like "Hey bud, I'm going on this work trip and I have a few days at the end... wanna come for the weekend? You can have the other hotel bed and I'll split the airfare with you." It's fun for both of us that way, and a nice treat that they wouldn't normally be able to afford. You don't have to fly them anywhere fancy, either. "Hey, local art show this weekend and I have a couple of tix! Wanna come? My treat, but drinks on you." It doesn't have to be weird as long as there's no expectation of anything serious in return, you're not giving more than you can afford, and the friend is providing some sort of reciprocity in return – as measured in friendship, not in dollars. Maybe they make a kick-ass friendsgiving dinner with all your favorite things. Maybe they commit (finally) to that D&D campaign you've been trying to get them to join for the last five years. Maybe you've just known them for a decade and you really value their friendship, even though your incomes have drifted apart over the years. It doesn't matter. Good friends are worth it, within reason. Now, that CAN turn exploitative if you let it... but just don't be a doormat. If some person expects you to pay for all their drinks and outings every time you go out and never calls you up unless they need something, well, they're probably using you. But that's a pretty different situation from a genuine friend that you've known and treasured for a while who just happens to make less money than you. If you enjoy their company and can afford to bring them along somewhere, wouldn't it be fun for both of you?