Most dudes acutely feel the societal imperative to be able to provide. Plus it's been psychically ingrained that attractive, worthwhile women are expensive. It's rare you see a nice-looking lady with a guy whose day job involves picking coke cans out of garbage cans. Because of this, guys have a tendency to spend recklessly early in a relationship. For Christ's sake, why do you think companies rent Ferraris?
The logic for fellas fake ballin' breaks into two primary vectors: 1) after my apparent Rick James lifestyle impresses her, we will have sex and I don't have to talk to her again; or 2) my phony Rick Ross lifestyle will impress her so much that she falls in love with me and it won't matter when she figures out that I'm a middle-class guy who "says" he can really taste the difference between Dom and Veuve.
And I don't blame women for not pumping the brakes on this conspicuous-est of consumption. Who intentionally derails a sweet gravy train? New York mayor Mike Bloomberg might but everyone else loves gravy. However, it's incumbent upon guys—I don't think women spend beyond their means to attract men—to come clean financially after this spendthrift courtship phase. Right around the time the "honeymoon phase" gets deep-sixed is probably the right time for the money talk to happen. How To Talk About Money Without Getting Upset
This is a lesson I've barely incorporated into my own life. The last few women I've dated have out-earned me from slightly to substantially. However, that did not stop me from paying for the first date and being ready to pony up thereafter, without ever directly discussing it.
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One of these "relationships" was with a hedge fund analyst who never actually offered to pay for anything. I didn't resent it; I actually only even noticed it in the post-getting dumped analysis, and it served as a call action for me to continue to be generous but also less fiscally macho. Now, it'll probably take about four glasses of scotch before I can blurt out, "Hey, you know that tiny, mediocre apartment I live in? Yeah, that's more in line with my income. Still want to hook up n' stuff?" But, still, it'll be better having that out there. I'll let you know how it goes.