The Office contained a cleverly written scene that highlighted the on-going cultural battle regarding proper grammar.

There’s a good linguistic analysis here. Does it matter?

Depends. For most people, no. Grammar is the nemesis of many people (students, in particular). Most native speakers of English don’t understand why it is that they have to say certain things in certain ways, other than it “sounds right.” Most of the time that works fine, except when we have to do formal writing or a formal oral presentation - then we feel the need to put on our grammar hats. As I stress to my students, the most important overall skill they should walk away from college with is to be decent writers. Yes, a music professor stressing writing. Here’s why: if one can write well, it entails numerous other skills: gathering information, critiquing it, organizing it, and articulating it clearly. What does it take to get a decent job and do it well? On various levels, all that stuff.

Proper grammar should ultimately reflect careful thought for careful communication. Many think proper grammar exists to cause them grief and create “formality” (Andy’s argument from the video). To a degree, their write (I know, I just couldn’t resist the wordplay): a lot of English grammar rules come from Latin grammar being laid on top of English to make it more “proper” and “acceptable” to 19th century writers (that’s why we can’t split infinitives; actually, we can). It’s no wonder that a lot of these distinctions are lost in everyday usage - English has the ability to communicate just fine with many of the overlay rules dropped (”..to boldly go”; “Is he coming with?”; also note that Brits will say “orientated”, whereas Yanks say “oriented” - left to their own devices, most people will say the former, as I did years ago - it makes certain logical grammatical sense). Latin grammar is not the only challenge for English speakers - all languages just gradually evolve and morph over the centuries - it’s hard to keep track of it all.

Good writing and speaking should require effort and thought; it should not be easy. If worrying about grammar gets people to slow down and think more carefully about their words, that’s a good thing. Easy too often makes for vague or regrettable words.