See, that's kind of the mentality I'm talking about. If you are going out in the first place, we can assume you like the people you are going out with, otherwise why are you going out? So, lets assume at this point you are going out with friends. Lets then assume you do this maybe once a month? Hell, lets assume twice a month. Now, lets say you have 50k saved up, and make roughly 2k a week. Lets also assume you can be pretty sure your friends have nothing saved up, or at most a couple thousand, and you know they each make maybe $500 a week. The average dinner bill is going to be around $100.
At that point, even if you payed for every meal, every time, you would be out just over 1 weeks worth of pay per YEAR. That in no way is going to harm your finances. If you limited it to once a month, or just payed every other time, you would be out only a couple of days worth of pay per year. In return you are able to spend all of that time with good friends who might otherwise not be able to afford spending that time with you.
I say this from a position of being the most well off of anyone I know. If I invite people out, I tend to throw in "Hey, do you want to go down to the the wine bar for dinner and drinks, on me?" because I know that otherwise the answer will be no, or that they will say yes and spend money they don't really have. Now, if I don't feel like carrying people, I simply don't invite those people, or I don't go out. No one is "guilt tripping" me, I honestly feel like having good times with friends is worth a certain financial cost to me. To me its no different that buying board games, or hosting parties. No one else I know can afford it, we all enjoy it, I can afford it, so I do it. I don't have too, I like too.
I'm saying that I buy a round of drinks and am out $30 and in my head I think "Ok, $30, that's an hour of work for me, no big deal", while I have been out with a doctor who make $36,000 per two weeks (That was his take home check after taxes), who said "Well, I only had one glass, do I need to pitch in $5 or something?" about a $36 bottle of wine, of which he had drunk a 3rd (3 full glasses between 3 of us). I said "Don't worry about it, it's on me.", and secretly went "What a fucking asshole" as he's the one who invited us out in the first place.
I guess its established that I'm often too nice, and get walked on as a result. I tend to trust people, and hope that everyone would act in a way that makes other peoples lives better having encountered them. I genuinely try to make sure that people are in a better mood after having encountered me than they were before. I'm not always successful, but I think if you took a poll of people who know me, they would say something to the effect of "Mikel is the happiest person I know, he's a joy to be around". Money is just another means of accomplishing that to me. I get annoyed when people have more than they could ever use, and hoard it for no reason, when giving a little bit here and there would make a lot of other peoples lives much better at little to no cost to themselves. /shrug
