As the staff’s resident relationship guru—who’s carved out a space on the web with an award-winning site called Naked With Socks On—I’ve been tapped by JET’s EIC to offer up dating advice and perspective each week for our readers. Five days out of the week I’m slaving behind a desk as JET’s Managing Editor, so I look forward to exploring the sights and sounds of Chicago with my wife as part of our weekly outings. I am Anslem Samuel Rocque and this is Date Knight.

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I’ll go out on a limb and assume that most people were brought up with the same ideals about dating and how gender roles play into them. While some have stood the test of time as steadfast guidelines that steer us on the right path, there are others that are simply just outdated. Among one of the questionable dating “rules” I’ve encountered over the years is the belief that men should pay for the first date.

Now, before I continue, let me be clear that I am in no way suggesting that men not be gentlemanly, but the idea that a woman should eat for free just because she is a woman needs to be retired. Here are my reasons why:

For starters if this is indeed a first date then chances are this woman is a stranger and someone you are getting to know. With that said, why should a complete stranger be given automatic access to the contents of a man’s wallet? I believe that going Dutch on a first date would make much more sense to all involved parties.

Every time I’ve expressed this philosophy, the women within earshot are quick to balk at the idea and call me “cheap.” The fact of the matter is I’ve paid for more than my fair share of first dates over the years—primarily because that’s how I was raised—but my rational self fails to see the logic especially when the outing doesn’t blossom into a significant courtship. She leaves the table feeling full, while I step away with my wallet feel empty. If you’re a single guy with an active social card these can lead to a series of false starts that comes with a hefty price tag.

I know better than to suggest a woman pay outright for a first date, but when the idea has come up for argument’s sake women have often said, “Whoever asks should pay.” Sounds fair enough, but whenever I ask a woman if she’s ever ask a man out, the response is very rarely in the affirmative. So we’re back to square one with men getting stuck with the bill simply because they are men who happen to ask women out because they refuse to do the asking. Suddenly the “fairness” of this dating rule begins to fade away.

Some women have countered my argument by saying that they’d be more than happy to pay for the second date. Problem is there’s no guarantee of such a thing happening if the people are not compatible. So again men are forced to lead blindly with their wallets. In response I say going Dutch is a more suitable approach to first contact.

Here you have two people who for all intents and purposes don’t know each other so if they both pay their way equally they can leave the table just as they came with no obligations or pressures. This negates the horror stories we’ve all heard where a man expects something simply because he paid for a lobster dinner. In this scenario two people can genuinely access each other and then determine if they wish to explore courtship any further and if so the original man-pays dating rules can be reinstated in good faith. I’m sure there are many skeptics but don’t knock it until you try it.

Do you think it’s fair that a man always pays for the first date? Do you think that going Dutch on an initial outing makes more sense? Or, is it the most ridiculous thing you’ve ever heard?

Speak your piece…