You don't mention his age, but it could also be about his dateability. I'm mid 40's and if (heaven forbid) I was single again, I'd be financially secure - and frankly, I'd want a man who was also financially secure. He doesn't have to be rich and not to pay for me, but simply a financial equal. There's too much risk in being with a guy who doesn't have his finances sorted out. Therefore; if he's of an age where women want to see financial security, then it makes sense that he's not getting out there.
However, if I was 20 years younger and just starting out - all I'd care is that he has sensible spending habits with what little he has.
Never regret anything that has happened in your life. It cannot be changed, forgotten or undone. So, take it as a lesson learned and move on.