One way to make the huge jump between being an intermediate and an advanced student of Japanese is to try to rely less and less on English. This is not going to help your ability to translate into English, but that’s not the goal. The goal is to jettison English all together and become able to communicate in Japanese alone, and if you can start defining new words in terms of things you already know, using a Japanese dictionary, you will rapidly be able to increase your comprehension.

I’m going to give you an example. Here is a four-character compound: 慇懃無礼. I can’t remember where I first learned it. I have a feeling I read it in a story somewhere.

When I read it, I looked it up in a Japanese dictionary, thought the definition would prove an interesting example to dissect, so I pasted the definition in my “to write about” list.

At this point in time, I don’t know the pronunciation of the whole thing, nor do I know the meanings of the first two characters. The last two characters are pronounced ぶれい and mean “rude” or something like that. Now, here’s what the dictionary told me:

慇懃無礼　〔名・形動〕表面はきわめて丁寧だが、実は横柄であること。「−な態度」

As in English, the first thing the dictionary is going to tell you is the part of speech. Here is a list of Japanese parts of speech:

名詞（めいし）– noun

動詞（どうし）– verb

形容詞（けいようし）– adjective

副詞（ふくし）– adverb

接続詞（せつぞくし）– conjunction

前置詞（ぜんちし）– preposition

助詞（じょし）– particle

So, 〔名・形動〕shows us that this compound can either be a noun or an adjective…I think. To be completely honest, I’m not sure what 形動 means at the time of writing, but it looks like adjective to me.

Now, let’s skip to the end for a minute. 「−な態度」shows us exactly what kind of noun/adjective it will be. It is showing us that it modifies another word via 〜な, just as 静か、貧乏、and 有名  (look ‘em up!) do.

One more step back and we see that the actual definition itself ends in こと. This, simply, is a word used to nominalize (turn into a nominal/noun) whatever comes before it. It’s basically an ~ing, but you need to get comfortable thinking of it separate from English. It is a こと, that’s it.

Now for the meat of the definition: 表面はきわめて丁寧だが、実は横柄である.

Let’s space it out a bit for beginners: 表面　は　きわめて　丁寧　だが、実は　横柄　である.

I knew the meaning of all but one of the words, so it wasn’t too difficult for me to understand, but I’ll give you a moment to look up all those words.

Okay.

表面 means surface, 丁寧 means polite, and きわめて modifies polite. Perhaps you’ll recognize きわめて if I give it to you in kanji? 極めて. Ring any bells? That’s correct – it means “extremely,” so the first clause of our definition means, “The surface is extremely polite.” (I know I’m being a bit hypocritical here by actually translating it for you when I previously said that you shouldn’t be translating, but for the purposes of showing you how I utilized this dictionary, I think it’s okay, and it would be rude for me to say, yup, there it is, go look it up, dumbass.)

だが is the connection between the two clauses and it means but or however. 実は means actually, and I’m honestly not sure what 横柄 means, but I do recognize the kanji. The first, pronounced よこ, you may recognize from the city Yokohama. It means side. The second is pronounced がら, and I recognize it from the word 人柄, which, I think, means personality or something like “type of person.”

So let’s think about what we do know: we know that this phrase so far means, “on the surface level very polite, but actually ____.” Because the way this sentence is structured, the number of words that fit in the blank are very limited. We can automatically cross “friendly,” “about to share a bounty of donuts,” “naked,” “holding two guns in the air,” and “sleeping” off the list. In reality we’re limited to opposites of polite, and, as I mentioned before, I did recognize that 無礼 means something like rude. 横 means side, so we can take that into account and assume that 横柄 must mean something similar to the opposite of polite and almost backstab-by/devious in nature.

Take into account the こと and our final definition looks like “being polite on the surface but actual disliking.”

I’ve just checked the definition in alc.co.jp and it gives “feigned politeness” as the much more economical answer. Well, I was close, and if I could remember the context of the story, it might have helped me narrow the definition even further.

Here’s the moral of the last 1000 words you just read: use a Japanese dictionary, rely on contextual clues, readreadreadread, and don’t be fussed if you can’t understand every coddamn word.