Don't worry about it, move on OP, it's her loss..

What kind of an asshole says such a thing. Just because she happens to not have a house atm doesn't mean she HAD to accept your offer or that she has to like you. And it sure as hell doesn't make her less of a person for you to assume she'd say yes just because she's homeless and you're not.

It seems a bit rude to use the word 'even', as if she's inferior to you or easy because she's homeless. I get that she'd be more likely to want to be bought food than someone with more money but I don't know, the way you've worded this is a bit off

I think your heart was in the right place, but I wouldnt fault her for declining. Depending on how you said it and her mood (being homeless mood not good) she eitehr thought you were planning of taking advantage of her, or that she was getting patronised. There is no win situation here. Problably harder to get her to dinner then a random single woman because of it, so dont think of the decline as the worst ever, because it never was an easy sell.

You are a real ass for the way you ended this FML. Sure the idea was nice but it went down hill fast when you said you can't even get a date from a homeless person. Who said she needed to go to lunch with you? Do not presume she needed to go with you because she is homeless. I can see why you are forever alone. You are an entitled piece of crap.