Ask a Bougie Chick: I can't afford her

For the rest of this week, we're still playing catch up on some Ask a Bougie Chick questions. Enjoy the goodness of OPP (Other People's Problems). Below, a troubled young man writes in...
Hey OneChele,
I'm 30, single black male living in Charlotte. I've been seeing a woman a few years older than me for about five months now. I knew when we first hooked up that she was used to going out with guys with a lot of money. I get that doesn't make them better them me, it's not about that. It's that even though she doesn't say it, I can tell she'd rather be going to nicer restaurants and stuff like that. 
We just got back from a vacation in Mexico and when we checked in she kind of looked around the hotel like it wasn't what she was expecting. One time I had to stop in the middle of ordering because she asked for a $60 bottle of wine. I can't afford that! I try to step it up and do nice things but I'm on a limited budget and will be for a while. I'm back in school and working full-time. 
As much as I like her and feel we are compatible in many areas, I just can't afford the things I know she wants. Should I just walk away now before I get in any deeper? I notice in a lot of your stories, you haven't been able to make it work with guys that don't have money - should I just date women who understand my money issues and keep it moving?
-Gerald in NC
Hey Gerald, 
Let me start on defense - how did this become about me? Please don't make dating/life decisions based on Chele's BougieTales of Dating Woe. I have dated men of all income brackets. Dating gentlemen with money struggles has not worked out for me but generally not because of the finances. As a friend of mine used to say: if the romance ain't right and the finance ain't tight, we can't take flight. Catchy but the point is that if the relationship isn't working and then you throw money problems on top of it - it's a recipe for disaster.

Now about your situation: this woman knew you weren't ballin' when you met her, right? There's got to be a reason she's not dating those other guys anymore. She saw something in you beyond your wallet, I must assume. What does she do? How is she funded? Might I suggest that if she wants a $60 bottle of wine that she knows you cannot afford, she purchase it herself or go back to dating fellas who can afford that? Are ya'll splitting any checks? Have you discussed any of this with her? 

Best case scenario, she doesn't realize that she's making you feel this way and you need to let her know that it is what it is. Since she hasn't overtly said anything, maybe she's not keyed into your struggle? Worst case scenario, she's used to certain things and assumes you'll find a way to get them for her regardless of paycheck. Either way, how much do you like her? Is this something you feel you can talk out/work out? If the answer is a lot and yes - then have the discussion and hang in. If not, you already know what to do. There are plenty of women who would be sufficiently impressed that you found a way to whisk them off to Mexico that the wine list will be the last thing they are worrying about...

BougieLand - what say you? What to do if a man can't "afford" his woman? Should the woman step up? Or get real? What are your thoughts about dating across widely disparate economic brackets? Do share...