LuvDoc,
A guy I am considering dating recently told me he stopped going out with a woman because she didn’t know the difference between “you’re” and “your.” I’m not illiterate, but I’m not a grammar Nazi either. Do you think it would be a mistake to go out with him?
– Misti

It would be a mistake to go out with him if you don’t want to date a man who knows what he wants. Clearly he wants to date a woman who knows the difference between a second person possessive adjective and a contraction. He’s going to do OK. There are a lot of women out there who understand that distinction. This is not to say, of course, that even the most vigilant grammarian isn’t prone to the occasional slipup. Who hasn’t blindly typed one when they meant the other? However, consistently confusing the two might imply a certain lack of sophistication that some people might find unattractive.

On the other hand, women who don’t know the difference between “you’re” and “your” are probably statistically much more likely to know how to change a tire, load a squirrel gun, or bait a treble hook with a big, fat, tobacco spittin’ grasshopper, so there’s a trade-off. Sophistication isn’t everything. Comedian Ron White has a whole routine built around the idea that you “can’t fix stupid,” but the truth is, stupid is one of the things you actually can fix; it just sometimes takes a monumental amount of patience. Patience is fine for some doe-eyed optimist in his late teens or twenties, but having to revisit the fundamentals of grammar as a quinquagenarian (if you don’t know what that is, we are TOTALLY not dating) is a bit daunting to say the least.

Even if this fellow isn’t a quinquagenarian pessimist, he might simply prefer women who don’t wear sleeveless, crop-top Ozzy Osbourne T-shirts, whose arms aren’t pockmarked with meth scabs, and whose mascara doesn’t run every time they hear Uncle Kracker’s cover of “Drift Away.” And you know what? That’s his right. Of course, the trade-off is that he might never meet a woman who will sport fuck him on the tailgate of a Gator in the middle of a javelina hunt and that would be a travesty. So, the question you need to ask yourself Misti, is not whether you should go out with him, but if you even want to.

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The Luv Doc graduated without honors from the University of Texas in 1988, receiving a BA in English, his first and only language. He has received numerous awards and accolades including but not limited to: A blue ribbon for being best on the balance beam in kindergarten at Louverture Elementary in Wichita, Kansas; the "Big Stick" award for the hardest hitting defensive player on the Norman High School football team in 1983; and three consecutive Austin Music Awards for "Best Country Band" in 2014,...