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► 動詞
苦労  [(1)くろう]  [苦労する]    meaning:  difficult  rank: 1
☆ 技術開発してもっと苦労したですか? ⇨ What was the point you had the biggest difficulty during the development of the new technology?

応える  [(3)こたえる]  [coll]    meaning:  difficult  rank: 2
☆ 猛暑に応える ⇨ The heat wave is hard on my body  (☛ Physically or mentally hard)

難航  [なんこう]  [難航する]  [liter]    meaning:  difficult  rank: 3
☆ 救助作業は難航している ⇨ The rescue operation is having a lot of difficulty  (☛ Literally “difficult navigation”)

難しがる  [(5)むずかしがる]    meaning:  difficult  rank: 4
☆ 皆難しがったが簡単だと思った ⇨ Everybody said it was difficult but I found it easy

► 成句
始末  [(1)しまつ]  [始末に負えない]  [coll]    meaning:  difficult  rank: 2
☆ あいつはどうにも始末にえない ⇨ He is just impossible to deal with  (☛ About something annoying to deal with)
☆ 燃料倉庫火事になって始末にえなくなった ⇨ The warehouse of fuel had a fire and it went out of control  (☛ About something annoying to deal with)

  [て]  [手に負えない]    meaning:  difficult  rank: 2
☆ 山火事は手にえない状態にあった ⇨ The wildfire was too much to handle
☆ 手にえない子供 ⇨ An impossible child. A child impossible to handle

  [て]  [手が焼ける]    meaning:  difficult  rank: 3
☆ うちの息子には本当に手がける ⇨ My son burns my hand, causes a lot of problems  (☛ Usually only refers to a person)

  [(2)ほね]  [骨が折れる]    meaning:  difficult  rank: 3
☆ 子供てるのは本当に骨がれる仕事だ ⇨ Raising children is a job that really breaks your bones, it is difficult

  [いばら]  [茨の道]  [liter]    meaning:  difficult  rank: 4
☆ 人生は茨のだった ⇨ His life was a road through thorny plants, filled with difficulty

断腸  [だんちょう]  [断腸の思い]    meaning:  difficult  rank: 4
☆ 

背水の陣  [(6)はいすいのじん]    meaning:  difficult  rank: 4
☆ 〇勝彼等は背水の陣をいた ⇨ Lead by 0-3, facing elimination, they took a position facing a river. They got ready for a fight to the death  (☛ An allusion to the story that Chinese army once fought and beat the enemy with a river behind, making retreating impossible even if they wanted to)

骨折り  [ほねおり]    meaning:  difficult  rank: 4
☆ 骨折りのくたびれけ (ほねおりぞん) ⇨ Broke bones and only earned tiredness. Bust your butt for nothing  (☛ A common phrase)

► 名詞
苦労  [(1)くろう]  [苦労人]    meaning:  difficult  rank: 1
☆ 彼女大変な苦労人だ (くろうにん) ⇨ She has gone through a lot of hardship

難しさ  [(3)むずかしさ]    meaning:  difficult  rank: 1
☆ てるのにの難しさがある ⇨ Raising boys and girls have different challenges

困難  [(1)こんなん]  [liter]    meaning:  difficult  rank: 2
☆ 計画実現にはくの困難が伴った ⇨ Many difficulties accompanied the realization of the project

絶体絶命  [ぜったいぜつめい]    meaning:  difficult  rank: 2
☆ 絶体絶命の危機 ⇨ A crisis with no escape  (☛ Literally “end body end life”. An extremely difficult situation that leads to death)

逆境  [ぎゃっきょう]    meaning:  difficult  rank: 3
☆ 人生で逆境というものを経験したことがない ⇨ He has never experienced any adversity in his life  (☛ Literally “counter situation”)

苦難  [(1)くなん]  [liter]    meaning:  difficult  rank: 3
☆ 苦難に満ち人生 ⇨ A life filled with adversities

修羅場  [しゅらば]    meaning:  difficult  rank: 3
☆ はいくもの修羅場をくぐりけてきた ⇨ He has gone through numerous extreme situations, hell  (☛ The Buddhist mythical place where gods battle)

試練  [(1)しれん]  [liter]    meaning:  difficult  rank: 3
☆ くの試練を乗り越えてきた ⇨ He has been overcoming many adversities  (☛ Difficulties that test your character and ability)

難関  [なんかん]    meaning:  difficult  rank: 3
☆ あの大学競争率の難関だ ⇨ That college is very difficult to get in with an acceptance rate of 1:100
☆ 津軽海峡世界の難関の一つだ ⇨ The Tsugaru strait is one of the most difficult waters (to swim across) in the world

難航  [なんこう]  [liter]    meaning:  difficult  rank: 3
☆ 交渉は難航が予想される ⇨ The negotiation is expected to be difficult  (☛ Literally “difficult navigation”)

荒波  [あらなみ]  [荒波に揉まれる]    meaning:  difficult  rank: 4
☆ 社会の荒波にまれたことがない ⇨ A person who have never been tossed around by the rough sea, experienced the tough reality of society

辛酸  [しんさん]  [辛酸を嘗める]    meaning:  difficult  rank: 4
☆ あいつのせいで辛酸をめさせられた ⇨ I was made to lick acid, go through a tough time, because of him  (☛ Literally “hard acid”)

難局  [なんきょく]    meaning:  difficult  rank: 4
☆ 我々とか難局を乗り切った ⇨ We somehow managed through difficult circumstances

難度  [(1)なんど]    meaning:  difficult  rank: 4
☆ 難度の体操 ⇨ A gymnastic move of high difficulty

八方塞がり  [(5)はっぽうふさがり]    meaning:  difficult  rank: 4
☆ 事業は八方塞がりになってしまった ⇨ The business has no more recourse  (☛ Literally means “eight corners all blocked”)

一山  [(2)ひとやま]    meaning:  difficult  rank: 4
☆ 仕事取敢えず一山越えた ⇨ We have gone over one hill, difficult part, of the work

臍曲がり  [(3)へそまがり]    meaning:  difficult  rank: 4
☆ へそ曲がり ⇨ A difficult, argumentative, old man

偏屈者  [へんくつもの]    meaning:  difficult  rank: 4
☆ は偏屈者だから付き合れない ⇨ I cannot deal with him because he is so difficult, narrow-minded

分からず屋  [わからずや]    meaning:  difficult  rank: 4
☆ あいつはとにかく分からず屋だ ⇨ He is impossible to deal with. He has to say no to everything  (☛ Literally “person who doesn’t understand”)

► 形容詞
きつい  [(2)きつい]  [coll]    meaning:  difficult  rank: 1
☆ 工事現場仕事はきつい ⇨ The work at construction sites is physically demanding
☆ 毎日10キロ走るのはきつい ⇨ It is tough to run 10km every day
☆ 精神的にきつい仕事 ⇨ A mentally draining job

厳しい  [(3)きびしい]    meaning:  difficult  rank: 1
☆ 彼等優勝は厳しくなった ⇨ Their winning the championship has become unlikely

苦しい  [(3)くるしい]  [coll]    meaning:  difficult  rank: 1
☆ この仕事明日までに仕上げるのはちょっと苦しい ⇨ It is a little too difficult to finish this work by tomorrow
☆ 会社経営が苦しい ⇨ The company is in financial difficulty
☆ が苦しい ⇨ It is hard to breathe. I am having a trouble breathing  (☛ Physically difficult)

辛い  [(2)つらい]    meaning:  difficult  rank: 1
☆ 両者まれて辛い立場有る ⇨ He is caught in the middle of the two and in a difficult position
☆ 一人生きていくのは非常に辛い ⇨ It is mentally very difficult to live life alone  (☛ Mentally difficult)

辛い  [(2)づらい]    meaning:  difficult  rank: 1
☆ この教科書解り辛い ⇨ This textbook is difficult to understand  (☛ Usually interchangeable with ”にくい”)
☆ この錠剤き過ぎて飲み込み辛い ⇨ This pill is too big and hard to swallow  (☛ Usually interchangeable with ”にくい”)
☆ ぎて読み辛い ⇨ The letters are too small and hard to read  (☛ Usually interchangeable with ”にくい”)
☆ 画面反射して見辛い ⇨ Light is reflected on the screen and hart to see  (☛ Usually interchangeable with ”にくい”)

難い  [(2)にくい]    meaning:  difficult  rank: 1
☆ この教科書解りにくい ⇨ This textbook is difficult to understand
☆ この子供けないようににわざとけ難くしてある ⇨ This lid is made intentionally difficult to open for children
☆ このろが見難い ⇨ It is hard to look what is behind in this car
☆ 聞き難質問 ⇨ A question hard/awkward to ask

難しい  [(4)むずかしい]    meaning:  difficult  rank: 1
☆ はとにかく難しいだ ⇨ He’s a really difficult person to deal with
☆ 難しい問題 ⇨ A difficult problem
☆ 難しい状況 ⇨ A difficult situation

険しい  [(3)けわしい]  [liter]    meaning:  difficult  rank: 2
☆ 会社前途は険しい ⇨ The path forward for the company looks very rough, difficult

難しい  [(4)むつかしい]    meaning:  difficult  rank: 2
☆ 彼女が難しい ⇨ She is difficult to please  (☛ An alternative pronunciation of むずかしい)

難い  [(2)かたい]  [liter]    meaning:  difficult  rank: 3
☆ それは想像に難くない ⇨ It is not hard to imagine  (☛ Usually used in negative as 難くない)

難い  [(2)がたい]  [liter]    meaning:  difficult  rank: 3
☆ のしたことはとてもし難い ⇨ What he did is difficult to forgive
☆ 本当だとはじ難い ⇨ It’s hard to believe it’s true

世知辛い  [(4)せちがらい]    meaning:  difficult  rank: 4
☆ ああ、なんて世知辛い世のだ ⇨ Uhh, what a cold, bitter, ruthless society this is  (☛ Difficult to live due to lack of compassion)

► 形容動詞
大変  [たいへん]    meaning:  difficult  rank: 1
☆ この仕事思ったよりずっと大変だ ⇨ This work is much more difficult than I thought
☆ 一人子供を三人育てるは大変だ ⇨ It is very difficult to raise three children all by yourself

困難  [(1)こんなん]  [liter]    meaning:  difficult  rank: 2
☆ この工事年内完了することは困難だ ⇨ It is difficult to complete this construction within this year

難解  [なんかい]    meaning:  difficult  rank: 3
☆ 相対性理論は難解だ ⇨ The theory of relativity is difficult to understand  (☛ Difficult to understand)

偏屈  [へんくつ]    meaning:  difficult  rank: 4
☆ 偏屈オヤジ ⇨ A difficult, grumpy, old man

► 連体詞
呆れた  [あきれた]  [coll]    meaning:  difficult  rank: 3
☆ 本当に呆れただ ⇨ He really is an impossible person  (☛ Someone difficult to deal with, especially because of his/her lack of responsibility)