>>33463461 (OP)
>pretend to be homeless or broke
Gonna be honest. Most women in general aren't gonna wanna deal with a homeless dude.
But putting that aside: pretending to be flat out broke is a bit much. Why not just go for...average dude? Not rich, not poor. Just a normal guy. That's a lot easier than taking it to the extreme.
Your concerns are valid. However it's on you to properly vet the woman. Dinner dates are bs. You don't get to know someone well while shoving food down your throat. Stick to something light like a coffee date. It doesn't cost much and you can spend more time relating than eating.
Next, you take her on date **doing shit you already want to do.** If you're into photography, like I am, you could take her out trying to capture some good photos and bring an extra camera for her. I'm into go karts so that's definitely some shit I'd be doing. Being fed isn't explicitly on the itinerary or even the main event. But it can potentially happen while you're out and about doing other things.
Why do this? It filters out women who are interested in YOU. A woman who likes you won't really care what the fuck you're doing, so long as you're there. A bitch who's a waste of time will be mad she's not directly getting "paid" for her time, because she really doesn't like you. She just likes what you can buy.
So yes, you can hide the fact that you have money. But don't take it to an extreme and be something you're not. There's a happy medium that protects yourself while also still being genuine. You don't want a fake bitch. So don't be fake yourself by taking this to the extreme.
Another thing: focus on what a woman DOES and not what she SAYS. A woman you shouldn't trust will say anything she thinks you want to hear. A genuinely good woman has the actions that follow those words. Lastly: do NOT project the fantasy of how you *want* her to be onto her. Be objective and look at her for who she is. THAT'S how you vet a woman.