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First of all, IMO, 5k 6k is considered quite a bit.
Second, you were a business person and your failure was not because your inability to continue the business. With that said, you have natural business mind set and if given another opportunity in the future, I am sure you will try again. Why not work towards that?
Third, if you feel you are not good enough for this girl and that because you think you can't satisfy her financial needs, why not do something that isn't finance related. Do something special for her, like once a week. If she really is the "it doesn't matter" type, you will see it (unless you are really bad at interpreting someone's feelings).
By doing something positive for her everyday, you will eventually feel like you can live up to her and call the shots. If it doesn't work, then you can at least tell yourself that you've attempted to.
Other suggestions I would give is, get in shape, get toned, get bulky, work out, try to get an awesome body that she can't resist.
Do something that she likes that isn't related to her. For example, if she's a charity person, start doing charity. Does she have a dog? Maybe you can do something for it. She'll appreciate you more and love you more for the person that you are.
PS - Condo, a car, and 5 - 6k monthly income, you'll be fine.
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