My first serious relationship I paid for everything. I was barely 18 and worked full time. Even still, just paying rent and utilities I was short, much less feeding us. I got my ex jobs, friends and family did the same. My ex quit or was fired from every single position. It took me years after dumping him to get my finances back on track.
I won't do that ever again. I won't be a mooch and anyone I'm with will not ever get to mooch. That being said, my partner makes more than four times the amount I do and he "only" has a high school diploma and various certifications. On the flip side, I initially started college when I was an age I cannot specify due to the ToS.
I never expected a first date with someone to be paid by the other party. I was always prepared to cover half. If someone offered, I did my best to accept gracefully and would then get the next date. In periods where I have been short on disposable income I could make up for it other ways, cooking dinner at my place, etc.
I have found in my many different life experiences that "success" can be defined in many ways. If someone wishes to be an artist and accepts the hardships that will likely entail, who am I to judge? I've been around absurdly wealthy/successful/educated and incredibly poor, "broken", and "uneducated" people. A balance of scholastic accomplishments and real life experience is lovely, but I am not so narrow minded or have a superiority complex (like some, not all, nor am I trying to call out anyone responding here), that I will look down on people without multiple degrees and don't pull in six figures.
Maybe between my life experiences, going from a fairly privileged upbringing to homeless in Detroit, to where I am now + being fascinated by humanity and anthropology gives me a broader view, but I can't say.
The long and the short is that while I most definitely still have flaws, I try to work on them. I admit I succumb to believing stereotypes at times, but I call myself on my own bullshit. I think my life is richer and better for knowing a wide range of people.