Chin up, maybe she just had high standards ;)

more like impossible standards...

Maybe if he would have persisted then she would have given in. If that were me my pride would have said no at least 3 times before I actually gave in to someone offering charity.

Offer the homeless man next to her the same deal so she gets jealous bahaha

not a good idea.

Just because she's homeless it doesn't mean she would go out with anyone that asks her

She's homeless.. not a prostitute

OP asked her to take her out for lunch, not for sex.

So because her life isn't going well she should go for any guy who asks her out, regardless of if she's attracted to them? It almost sounds like you're trying to prey on it with the way you worded this.

If she was sweet. Maybe she just wouldn't want to burden you.

Maybe she has her reasons. For example, maybe she felt like she was being pitied and didn't like it.

She was probably wary of strangers taking her out, out oc the blue. They have been probably been advised of human trafficking.

Now correct me if I'm wrong but sounds to me like you were trying to take advantage of her situation.

No one owes you a date, homeless or not. That being said I was once homeless myself and rejected everyone even if I liked them. I wanted to make sure I didn't accidently take advantage/get taken advantage of. Most people in that situation I've talked to felt the same. Don't take it personal.

Just how entitled can you get ? "I can't EVEN get [...]" Seriously ? Do you view her as inferior to you, or as "easier" to get because of her situation ? If you truly wanted to be nice, you could just have offered to buy her something without forcing a date upon her. Maybe she would refuse that too, and that's also her right !