Then those women are not your market. Why are you wasting time on them? You want a woman who has her own personal finances in hand but no respect for yours? How does that make sense?

As for the rest of your comment, you’re getting lost in the weeds. I think it’s an error to try to keep hard and fast rules. That limits options and compromise.

I’ll tell you some things I used to suggest or accept. As with all free advice, you’re free to do with it whatever you want. No skin off my back. Maybe if you don’t like these, they’ll get you thinking broader and lead you to things that will.

Normally I tried to date someone with a relatively equal income. But I didn’t exclude for it either. When dating guys who made significantly more than me: I’m always honest but unapologetic about my financial situation. The minute they get judgy or try to "help" me, I cancel. They are not the guy for me. One guy we alternated date responsibility. He did his normal. I planned low cost / high fun dates. I took him to symphony in the park, and packed a picnic, I took him roller skating, I took him fishing, to a local play, horseback riding, to the state park, on a bee survey, and to a Renaissance fair. Doing so really let him into my life more than the fancy dinner dates. He said it was the most fun dating he had had in years. Another guy, he didn’t like to be surprised and wasn’t very adventurous. For every 5 dates he payed for, I payed for 1 (he was truly loaded). Another one he paid for every date in exchange for me not giving him grief over having to cancel often (his ex had a habit of suddenly having emergencies with the kids).

I’ve also dated guys who made significantly less than me. One, I paid for every date. Another, we went dutch every time with the understanding that every date would be planned and if either of us couldn’t handle it, then they could reject and either reschedule or suggest an alternative. No harm no foul. One guy, we didn’t go out, we hung out. Mostly at my place because I have food and stuff to do and his mother got on my last damn nerve.

I actually wouldn’t recommend that last one because if you break up and they or their mother have a hard time embracing that fact, it’s not the best situation for them to know where you live and know your place well. Thank God for large dogs, with big dog bark, yeah?

So anyway, there’s options. Lots of them. You just have to be creative. And anyone who doesn’t respect your wallet and your
boundaries is not someone you want in your life anyway. Look for somebody real, not someone performing.

When I was a kid, my grandfather was a banker so he took it upon himself to teach all of us grandkids about money. To be honest, a lot of it was kinda sexist past an era where women can have their own bank accounts.

Anyway, he had this thing about how a man kept his wallet. If it was tidy, all the bills kept crisp, turned flush, and in order, that meant he most likely had his finances in order. If he didn’t he had poor discipline, management skills, and self respect. He said men could hide their financial situation for a while behind debt to try to impress a date and that was unfair to women as well as a further indication of his lack of self respect. Because he’s lying, right? So he said if a guy is wining and dining you, casually take a peek at his wallet when he opens it and see what kind of shape it’s in. Then you know what you’re dealing with. Further, any guy who has to pretend like that, is not somebody who’s going to be steadfast and calm when things go bad. He’s going to be someone unpleasant, histrionic, raging, out of control, and dead weight.

Papa was a smart man.

I’m not trying to be judgy here or make accusations. I’m just going off some of your comment which may or may not be from personal experience. K?

If your self esteem is so low that you find yourself self sabotaging your finances tryinf to impress a woman who clearly does not deserve to be impressed, you should do two things before dating.

1. Work on slaying some of those martyr dragons and regain some self respect. You’ll be glad you did. Your value as a human being is not in how much money you make.

2. Learn to see people for who they truly are. Keep your circle tight and don’t waste time on dead weight people who do not add to your life. That’s also not about money. It’s about finding people who love you authentically and completely. People who bring out the best in you.

I’m done bending your ear now. Best of luck.