Well, “of” and “‘ve” shouldn’t sound identical. Unless you are totally dropping the vowel sound in “of”. Though it’s common for people to do so, I probably even do it at times.
So in that situation, “should’ve” and “should of” would sound identical.
By the way, I’m posting this on my phone and it’s actively fighting me, trying to correct what I’m typing here. My phone is a goddamn prescriptivist. 
“Alright” is fine and dandy in informal English, such as internet message boards. “All right” is preferred in standard English, and currently, there won’t be a context where it’s incorrect (emphasis on “currently”). Avoid “alright” in formal writing.
It would seem obvious that Resting Bitch Face is the passive voice, but I’m led to wonder if your great bitch face is considered active voice?
“Should’ve” and “should of” sound exactly the same to me, and it’s not me dropping the “o” in “of” but rather adding a schwa between the “d” and “v” in “should’ve.” I’ve never heard it said with the “d” rammed straight into the “v.”
It’s the least I could do. If I could have done less, I would have.
For me it’s the difference between “shoo-div” and “shood-uv”.
The “oo” pronounced like “good” not “food”.
Yeah, the former is not how I’d pronounce “should’ve”. A short “i” sounds weird to me there in my dialect. Britannica has if as a schwa:
Disagree. The word “of” is almost never stressed, and when unstressed, the already weak vowel will be further reduced to nothing by most speakers. And that is what the apostrophe in 've indicates: a completely reduced vowel.
The whole reason people write “should of” is that they hear the 've of should’ve as the word of. (Or, as I suspect, it started out with “shouldn’t of” or “I’d of” or similar, as there is a resistance to double contractions in written English.)
Obviously you’ve never seen Beck’s RBF. It’s active enough she could turn you to stone. 
With which phrasing, then, shall I use whomsoever?
(Runs from @Monty’s wrath)
(Edit: runs even faster when I see the age of the post to which I am replying.)
When I verbalize “could’ve” and “could of” there’s a difference. It’s subtle but it’s there. There is an “uh” in “of” that’s not there in “could’ve”.
Then again, there is a weird accent we have up here supposedly, like how we pronounce “egg” with a long “a” sound which I thought was how everyone pronounced it.
The correct way to use this valuable word was illustrated in a scene in an old British sitcom. When the front doorbell rings in an aristocratic English household, the butler and the footman are occupied with other tasks, so it falls to the hapless lowly boot boy to answer the door. When the caller announces who they wish to see, the boot boy draws himself up in a posture of as much regal dignity as a lowly boot boy can muster and inquires “whomsoever shall I say is calling?”
The scene also illustrates the correct response to this inquiry, which is to say “I’m Lord Shawcross, you idiot!”, push the boot boy aside, and stride into the house. In 1920s English aristocracy, protocol was everything! 
But you can work the probabilities. Which is why people adjust their register on fly, typically unconsciously. Set it too low and you sound ignorant. Set it too high and you piss people off, especially in the US.
You can work the probabilities stupidly and ignorantly, relying solely on your instinct and ignoring way humans perceive patterns that aren’t there or more generally the way they suck at probabilities. IOW I agree that it’s generally best to dial back your preconceptions, especially when entering a new social environment.
I suspect some of your peers were expressing their inner grammarian, the one that diligently corrected their own missteps. A few may have been assholes though.
Communication is hard. Couldn’t I have made the above points with fewer words? I tend to go long and actually admire posters who are better at brief and direct language.
I agree with all of that. I will add, though, that it’s usually possible to tell without too much difficulty if the speaker (or writer) is just speaking casually and deliberately being colloquial and informal, or if they actually have poor language skills. It may require a reasonable sample size, but usually the information is there.
One way to tell – and this goes back to a point I’ve made several times – is that there’s a difference between being colloquial and informal and making obvious mistakes in grammar and usage. I don’t mean things like “could care less” which I object to only stylistically; I mean literally being ungrammatical in ways that aren’t attributable to dialect or idioms. One can look beyond grammar to vocabulary and stylistic markers. And beyond all that to the actual ideas being expressed.
For example, the speech of George W. Bush was consistently full of malapropisms, mangled language, and unintentionally comical sentence structures. He couldn’t help it. The man is an idiot.
And don’t even get me started on Trump, who barely speaks at the level of a fourth-grader, and not a very bright one. He can’t even maintain a coherent train of thought; his language meanders from one unrelated topic to another even within the same sentence, although he doesn’t even really use sentences at all and it’s usually difficult to tell when one pseudo-sentence ends and another begins.
Any hope of understanding what he’s saying is further confounded by a peppering of mysterious pronouns with no referents, so you don’t know what the hell he’s talking about. He has an extraordinarily limited vocabulary and knows only simple words. When he wants to be emphatic about some point that he wants his listener to remember, instead of using the oratorical device of reframing the point in different terms, he just repeats the exact same words several times, because he knows no other. Conclusion: moron.
And Michael Jordan’s golf game was terrible: he kept bouncing the ball instead of hitting it with a club, and instead of trying to get it into a hole in the ground, he kept throwing it through a basket hoop. If you count the number of times he struck the ball, he was like 5,000 over par in every game.
Judging Trump’s speech pattern as if he’s trying to give coherent, logically connected, honest speeches that read on the page like an essay is like judging Michael Jordan’s basketball career by the rules of golf. It’s a fundamental misunderstanding of what’s going on.
That doesn’t mean you can’t judge his speech. As I said before, there’s only one meaningful metric: is the speaker’s speech accomplishing their goals?
In order to make that judgment, you gotta figure out the goals. Trump’s goal isn’t to rival MLK or Obama or Lincoln or Clinton as a speechifier. His goal is to draw big crowds, entertain them, rile up their hatred and fear, and build a populist movement that might return him to the White House. He’s terrifyingly good at using language.
If you judge him by an irrelevant metric, you risk underestimating him and his capabilities. Judge speech accurately, and you’ll have a much better understanding of what’s going on.
Your point is spot on, but your analogy is flawed, since Michael Jordan can and does play competent golf.
Dammit, that’s what I get for using a sports analogy. Thanks for the heads up!
Think P. T. Barnum.
Great post, LHoD.
Prescriptive-adjacent grammarians definitely need to keep register in mind, especially in political oratory but also in common settings. Set it too high and part of the audience will resent you. Set it too low and another part of the audience will think you are an idiot, possibly because you are an idiot. We can’t rule that out.
But yes, Trump is very good at reading crowds, riling up crowds, and giving them a charge. The process is instinctive and has nothing to do with a command of policy details, something Trump has never had and has never shown any interest in. He’s a showman, but showmanship involves skilled use of language. It’s just a different a different skill set than is commonly taught in college or K-12.
So proper grammar depends on context.
I have a few issues with your points. I’m not going to argue with the self-evident truth that any language style that accomplishes its goal obviously has value. But surely you must see how limiting that judgment is? Someone who can only speak in one fashion and appeals only to a like-minded audience is not going to be able to appeal to other audiences, so the range of goals they’re going to be able to accomplish will be much more limited compared to someone who does have versatile language skills.
Let’s not get sidetracked on politics, but there are many complicated reasons that Trump may get re-elected and it’s certainly not because everyone loves him and he has the magical skill to able to connect with them at their own level.
But on the matter of his language skills, or rather the lack of them, remember I said at the beginning that one can usually make this judgment given a sufficient sample size. With Trump, the sample size is immense. And whether he’s speaking at his rallies, or being interviewed, or holding a press conference, or sending out Twuths with random capitalization, his language level is always the same. It’s the only language he knows. And while it may appeal to the adoring fans at his rallies, in other circumstances it invites ridicule.
On your Michael Jordan analogy, I didn’t know he was a good golfer, but I’m not surprised. To excel at his original sport he had to be athletically fit and well-coordinated. He’s more likely to be good at other sports than someone who’s terrible at all of them. The analogy with language skills here should be obvious.
I have another example of strong language skills being evident even in informal registers, and it’s one that you may find hard to refute. The example is: you. You love writing your posts here in an informal style, with liberal use of colloquialisms and the occasional neologism thrown in. Am I going to criticize you because “speechifier” isn’t a real word? No, because what shines through in your posts is the composition of someone with a mastery of language and confidence in its use. It’s not hard to tell, which was my whole point. Now, shrug that off!