夜眠れなくて彼は疲労して顔色が悪かった。

He was pale with fatigue after his sleepless night.

夜(よる)眠(ねむ)れなくて彼(かれ)は疲労(ひろう)して顔色(かおいろ)が悪(わる)かった。

Yoru nemurenakute kare wa hirōshite kaoiro ga warukatta.

夜 (よる、よ)

evening; night

彼 (かれ)

he; him; his; boyfriend

は (は)

topic marker particle; indicates contrast with another option (stated or unstated); adds emphasis

疲労 (ひろう)

fatigue; weariness

顔色 (かおいろ、がんしょく)

complexion; one's colour; one's color; countenance; expression; one's face

が (が)

indicates sentence subject (occasionally object); indicates possessive (esp. in literary expressions); but; however; still; and

悪い (わるい)

bad; poor; inferior; evil; sinful; unprofitable; unbeneficial; at fault; to blame; in the wrong; sorry

Readings: ヤ、よ、よる

Meanings: night, evening

Readings: ミン、ねむ.る、ねむ.い

Meanings: sleep, die, sleepy

Readings: ヒ、かれ、かの、か.の

Meanings: he, that, the

Readings: ヒ、つか.れる、 -づか.れ、つか.らす

Meanings: exhausted, tire, weary

Readings: ロウ、ろう.する、いたわ.る、いた.ずき、ねぎら、つか.れる、ねぎら.う

Meanings: labor, thank for, reward for, toil, trouble

Readings: ガン、かお

Meanings: face, expression

Readings: ショク、シキ、いろ

Meaning: color

Readings: アク、オ、わる.い、わる-、あ.し、にく.い、 -にく.い、ああ、いずくに、いずくんぞ、にく.む

Meanings: bad, vice, rascal, false, evil, wrong