More precisely, have a gigolo mindset.
Chances are you are thinking it is the man's job to pay for her time and attention she is offering you. And you would be more than happy to do so.
But a gigolo has women pay for companionship. Why would women want to pay a gigolo for companionship when they can have someone like you who will pay and listen to all her problems?
This is a where you need to change your mindset and ask yourself what would it take for you to become a successful gigolo?
1. Gigolo offers great companionship, great ideas and can lead because he has the experience and knowledge around his environment and is willing to take risk to learn new environments.
2. Gigolo is not embarrass to be with an unattractive woman because he knows he is helping her. A low self-esteem frustrated chump would feel embarrass to be with an unattractive woman because it is an indicator of his own beliefs that he is unworthy.
3. Gigolo knows when to walk away. It is not about the money, but her attitude. If she is gold digger, run fast. Leave her where she is and don't even bother driving her home. A low self-esteem frustrated chump will stay till the end. He will accept everything she throws because he is hoping by putting up with her, he can get some intimacy. The truth is gold diggers don't give intimacy. Gold diggers know once the intimacy is offered, the gold stops coming.
Your best bet is to find females that you can stimulate emotionally, first. And that is the skill you should aim to master!
Frustrated men think they have something to offer because they give women freedom. They think by letting women make the decisions, they would be appreciative and reciprocate. And when that does not happen, frustrated men become angry.
Woman don't need a man to give her freedom. She already has freedom.
Women want stimulus. Women want a man that has an idea as to where to take them, how to interact and how to stimulate her emotions.
That is, don't ask her what she likes. Don't ask her what she likes to do for fun. Instead, offer something to do. Offer fun things to do. Offer stimulating things to do.
To do that, a man must be able to go out there and experiment with new activities. See what's fun and see what works. Then, he has the experience and knowledge to offer these activities to others.
That is, take initiative, go alone and experiment. Once you gain the experience and consider the activity stimulating, bring a partner.
Being a provider is a distraction.
It distracts her from being turned on. No one ever gets turned on by being given money. But if you start paying for everything she wants, then her pleasure and focus is shifted from delight in you to greed and what can she get from you.
So should you ever offer to pay before intimacy? The short answer is maybe.
The goal is still to get her turned on. Not to have her focus or worry about the bills. The idea is that you want her mind to enjoy the interaction with you, not enjoy the fact that you are paying for everything. So as long as the pleasure of the interaction is still delight in being with you, than you are in the right direction.
Simply put, go to cheap places until she has proven herself.