I have taught Cicero’s writings for years.  If you are in Classical Conversations, that’s Third Year Latin by Robert Henle.

I was excited to teach the book… in the beginning.  I was discouraged to find that, after almost twenty years of teaching, reading, and studying Latin, I could barely make out what Cicero was saying.  You may be feeling the same.

We are not alone.  Years ago, Stephen Leacock admitted he had the same problem at the tail end of his own classical education.  Then, he nails it.  He pulls the curtain back on the official secret.

Check this out:

I revert again in conclusion to the objection that so many of us might make that we learnt Latin for years in school and college and never got anywhere with it, never got to be able to read it straight off. Of course we didn’t. Nobody ever does. Not even the professors; no, nor the Romans themselves, not in the way that we read English. This is of course a sort of official secret handed down for generations, and I am really violating here the obligation of my profession by divulging it. But perhaps the time has come to remove the veil. Hitherto it has been better for the world to pretend that at least somebody could “read Latin straight off.” Now it is better to have the truth. The Romans themselves couldn’t.

I am prepared to support this statement. Written language in Roman days, before printing and newspapers, was on a quite different footing from what it is now. There was the ordinary speech of ordinary people, jabbering away all day, just as we do now, with fragments of sentences, exclamations, phrases, false starts and short circuits. Except on the stage, conversation is never done out in full periods, unless by old maids, professors, and garrulous village philosophers; and done thus it is always either ludicrous or tiresome. But we moderns have a written language also of easy and rapid comprehension because we need it for the daily news and the love romances and the crime stories of which the Romans had no current supply. For them one love story had to last a thousand years, from Dido till the fall of Rome. So when they wrote, it was different. They took up the pen as a man puts on his Sunday clothes; they were not trying to be easily intelligible. They wanted to get the full effect, and expected it to take a few moments’ reflection to grasp it. I am quite sure that if one read out an oration of Cicero to a Roman who had never heard it he would soon get mixed and interrupt to say, “Read that last paragraph again, will you?” Just as you yourself would do, if someone read you a section of Browning without fair warning. The parallel is exact. Browning and Cicero were doing the same thing, proposing to sacrifice immediate comprehension for the sake of deeper comprehension when comprehended.

But, you say, some of Cicero’s writings were speeches made in court? Not at all; in court they didn’t sound like that, and they were retouched afterwards. A glance at the pages of the Congressional Record will show what is meant.

I remember once when I was a master at school giving a prize of a cake, specially made, with all sorts of icing and emblems—a joy to look at. The baker showed it to me and received my congratulations with obvious pleasure. But he was an honest man, and he said, “I’m not saying, sir, that it will be much of a cake for eating.” I assured him that no one would think of doing anything as brutal as that. So with the Roman writings—not much of writings for understanding.

All this I say by way of comforting those who, like myself, studied Latin for years and never were able to read it—unless we had read it already.

This is all from Leacock’s book, Too Much College or, Education Eating Up Life.  It’s free online.  If you don’t like reading digital books, here it is from Amazon: https://amzn.to/2GNsJDI