I'm having a hard time understanding this, and maybe someone can point me to some resources. I am pretty well off, have a great job, vacation twice a year, and generally like to have upscale / expensive dates. I'm trying to understand why everyone is recommending 'cheap and simple' first dates versus slightly more extravagant ones if its the 'norm' for me. What im saying is, if im not going 'above and beyond' what I 'normally socially do'.

I don't like cheap restaurants, and I only prefer upscale bars/clubs. What happens if the girl is higher class? You can't just take her to some backwater bar to show 'you dont really give a fuck'. Where do you draw the line? Should I adjust my budget to her lifestyle? I argue that you can connect with a woman regardless of location, and she is not going to see you any differently as long as you are not spending beyond what you would on an outing with guy friends. I only want to date women that enjoy my lifestyle.

I should note that im looking to date women / have relationships, not looking for one night stands.