In the end, individuals, not traditions, drive relationships
Q: I thought you were right on in your answer to B. from Maine (about who pays for dates). You were correct to suggest kindness. However, I think your answer was a little simplistic when you said, "Note that none of these (rules) is gender-specific," including, "If you ask someone to dinner, you pay." Let's be real, the rules are not gender-specific, but the rituals are. Who does most of the asking? Our culture's courtship rituals are based upon gender roles of previous generations. The man's role is the provider (paying for the dinners, dating, dancing, driving expenses and eventually diamonds).
What do you suggest men do in order to continue to be kind, but also not be expected to pay?
B. from Virginia
A: The only way any of us can change anything outside ourselves is for us to make changes inside. If you want women to pick up some checks, then date self-supporting, independent-minded women — or just date women who are givers, not takers, by nature. If a woman continually sits on her hands while you pay, then stop seeing her.
If those are the only women you ever find, then take a hard look at what you find attractive (and off-putting) in women. Ultimately, your own taste in women will have far more say in your rituals and romances than society ever will.
If you want women to do the asking, then make yourself accessible — easy to talk to, slow to judge, receptive to invitations and faultlessly immune to gender-baiting. If you think diamonds are archaic, then look around you. Women who see them as a waste of a perfectly good down payment aren't even cutting-edge anymore.
And if you think men have it bad in this area, then, instead of seeking knee-jerk justice for yourself, first find out whether cosmic justice hasn't long since beaten you to the scene. Men have to ask! (Women have to wait while someone else decides their fate, or risk looking "aggressive.") Men have to pay for dating! (Women have to wonder what men want from them — love, or sex?) Men foot the bill for diamonds! (Women foot the bill for weddings.) Men do all the work during courtship! (Women then get to do the man's laundry, dishes and vacuuming in perpetuity, and, oh, child-rearing.) Men have to be breadwinners, with all the pressure that entails! (Women have to depend on someone else to support them, with all the vulnerability that entails.) Capital-T Tradition doled out plenty of nonsense for each side.
Certainly a lot of these totems are already falling or have fallen. Still, anyone invested in further liberation from gender-based expectations would be served best by treating the opposite sex not as the enemy, but an ally.
The talk: You want individual circumstances, not societal expectations, to determine everything from who buys dinner to who becomes primary breadwinner or caregiver. The walk: Challenge and purge your biases in all areas, not just in dating, and value others who do the same.
If in the end you choose someone who has traditional expectations, or even if you decide you'd rather keep paying to keep dating while you seek out that like-minded soul, realize this is a choice you're making — not one Tradition forced down your throat.