I was approached by my (only) ex about possibly trying again, but once he found out that I was still making so little money, needing help to get by in life, etc., he dismissed me as not acceptable. I want to know why and how did the amount of money someone makes become such a big deal in a relationship?
Because the concept of Working & being able to At Least hold your own means something in a Relationship. You two already had one -- and he was pointing out the reason. Why go again, if a central issue was still there, ya know? I'm pretty sure in your situation, he wasn't expecting you to be some big career woman -- but instead, wanting you to be someone who isn't Dependent on a BF financially as part of your individuality. I think a guy would be willing to date a gal who isn't making it by so well -- but after Dating for a while he finds out That's the way she likes it, and it's not merely some temporary down period in her life -- he'll be turned off.
Your choices are:
1) get a career (which really is the best choice because marriage is no guarantee. Even if he can support you he could drop dead in a car accident and you are left with no income.)
Or "merely" a stable work record, with or without an Associates Degree (although the latter is probably the best option)... where you'll at least be able to support yourself consistently, even if living paycheck to paycheck if not being a real frugal person. Guys in the dating field in general don't ask for much -- just "Hey, you can hold your own."
2) lose weight and conform your body to the utmost conventional beauty standards in hope of snagging a wealthier guy to keep you home (and understand chances are he will replace you post kids since most men who care a great deal about looks burn through women like crazy always looking for hotter and younger)
Yeah, but a gal's options will still be limited. And getting to the point of getting a truly Wealthy guy -- many women can't do that by getting in good shape while expecting to never work to support themselves... unless they go really Low on looks of said Wealthy (much older) guy.... or more realistically a guy with a great paying job but certainly not Wealthy, but she becomes out of his league because he's sub-par on the looks.
IMO, I would say a gal with her mindset needs to come back to post WWII reality: There's no entitlement or value in the tradition of women being labeled as not having to support herself. It should be a value to herself as a human being to be able to. And with that said, strive to accomplish both #1 and #2 with some accomplishment -- and things will work out just great. But the main thing is the Entitlement mentality, which will turn too many guys off that she'd take a liking to.