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I voted for who ever asks for the date pays. I would say the same thing no matter who made more money. The only time I would say something different is if the more wealthy of the two changed the location of the date to somewhere the less wealthy person could not afford. In which case, he/she who changes the terms either pays for the whole thing or pays enough that the other person is only paying what they would have paid if the terms had not changed.
That's my idea of fair. It's what I was raised to believe. Sort of like with the opening of doors. It's not that the man should open the door for the lady, it's whoever gets to the door first should open it for the person behind them. In addition, younger/healthier people should always open the door for the elderly and handicapped. No need to make a big deal about it .... just do it.
If someone dead poor asked me out to eat at a taco stand, I would expect them to pay. If they asked me out to eat at a taco stand, and I suggested the Four Seasons instead, I would expect to pay and they could help with the tip if they offered.
Believe it or not, asking someone for a date is a verbal contract (everywhere that the English common law is in effect anyway), and you don't just go changing the terms without the other party's knowledge and consent. The opening the door thing .... probably not a contract, but certainly polite.
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