01/22/2014 01:36 pm ET Updated Mar 24, 2014

If You Don't Buy Me a Drink, I Won't Date You

As a recent transplant to Chicago from San Francisco, I've been faced with a number of questions regarding what Midwest cultural norms I'll have to adjust to, and whether doing so might mean compromising my own character.

As a fervent poor person, one of my biggest fears has been what it'd be like to date in the Midwest. You see, I recently had my first date with a local Chicago lady, and nervous, I asked a female co-worker for advice.

She warned me that women in Chicago are going to fully expect the man to pay for the date, and to not do so would demonstrate that I didn't truly like the woman. Conversely, in San Francisco it's fairly common that a man and woman will split the cost of the date, or trade off buying each other rounds.

The idea of going Dutch stems from a general sense of wanting to move towards equality for men and women, and also that I'm poor as fuck. It's worth noting that San Francisco's heavy gay population has also had an impact on dating norms, given that antiquated courtship procedures were never really instituted for the gay population, who historically have had to keep their dating away from the public eye.

Some women will claim that chivalry is dead, but that's generally when I make a pee-puddle and put her cardigan over it so that I don't get my heels wet.

If you look up the definition of chivalry, inherent in it is that those who are chivalrous are helping out those who are weak. And I don't date women who view themselves as weak or incapable. I hold open doors for women. I also hold open doors for men. I hold open doors for people because it's a nice thing to do, not because you have a vagina and that renders you incapable to do anything in the absence of a man.

Returning to my co-worker, she contests, "But a woman wants to feel like she's worth the price of the drinks!"

Wait, what? Are we buying women now? How many drinks = how much woman? Dating is tough, I get it. Women are inundated with all sorts of sordid messages vying for their affections on OKCupid or men in bars who they'd prefer not to talk to offering to roofie their drinks. But a system has evolved (and I realize there's plenty of evolutionary and historical precedent for this) wherein sex has basically become a commodity for females, bartered against the material possessions of men. And as a poor guy, it makes me cranky.

When money enters the dating equation, the lines between dating and prostitution start to get pretty blurred. Which by the way, I have no issues with prostitution, but let's stop wrapping it up in coy terms like "being a gentlemen" and "providing."

And let's be clear: everyone enjoys free drinks. I also like gravy waterfalls and blowjob machines, but my food stamps don't cover the latter. When you frame a conversation about dating by saying one side needs to "earn" the other's affection, it gets to be a pretty slippery slope of inequity. And let's not forget that along with the chivalry of yesteryear came lots of boozing, cheating, and abuse. I know, because a friend who watches Mad Men told me.

My co-worker acquiesces. "Alright -- I see your point. But I think that the person who asks the other person out on the date should be the one to pay. If I, as a woman, ask you for a drink, then I should pay."

Absolutely. Except when was the last time that happened? If the rule was "If I invite you, I pay. If you invite me, you pay," it doesn't sound like there's much incentive for women to flip the script here on their male counterparts.

Know this: when there's an expectation for each to pay half, so much of the anxiety of dating goes away. There's no more concern over things like how expensive the restaurant is going to be, you just split the entree and then enjoy as many free bread sticks as you want.

"Ladies in Free + complimentary glass of champagne!" nights are the fucking worst, and it really highlights the economy of sexual trade. The idea isn't complex: if an establishment creates fewer barriers to entry for women (insert joke here) and gets them a little drunk, that means there'll be a higher probability of sexual encounters for men, who in turn are willing to spend the money to get sex. If you don't believe any of this, please see Las Vegas trust me.

When women set an expectation that they are to be taken care of financially, it leverages the ability of any man capable of doing such to lack other character attributes. Effectively it's like buying an asshole pass (just tag to board!), which I've seen many times. Of course no man should be an asshole to any woman, just as no woman should be an asshole to any man. But expecting that someone's going to pay your way is kind of an asshole-ish move.

As it turns out: my dates were exceptionally cool. So far every woman I've met has at least paid partially for the date, if not half, and in an unprecedented instance (even by San Francisco standards) one fine young lady insisted that she pay for the entire fancy meal.

All of the dates prefaced actions by saying, "It makes me really uncomfortable that some women expect a man to pay. But I don't think I'm normal." And yet, so far that's been the norm. Well done, Chicago.

Of course the argument could be made that rather than women buying their own drinks (and fucking who they want to instead of having a dowry for their pussy), that men should take the first step and ensure that women are being paid equally in the workplace. I mean, sure.

For more opinions on sex and dating, listen to the latest Full Disclosure podcast with Chicago dominatrix Lady Sophia.