How to say he had a hard look on his face. in Japanese

1)彼(kare) (ok) that , or something understood without naming it directly)/that person/over there/hey/eh?/thatは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sigh難しい難しい(muzukashii) (adj-i) difficult/hard/troublesome/complicated/serious/fussy/particular/fastidious/hard to please/displeased/gloomy/glum/sullen/serious/dirty/unclean/filthy/detestable/unpleasant/uncomfortable/creepy/spooky顔(kao) (n) face/visage/look/expression/countenance/honor/honour/face/influence/notorietyつきつき(tsuki) (ok) deskを(wo) (prt) indicates direct object of action/indicates subject of causative expression/indicates an area traversed/indicates time over which action takes place/indicates point of departure or separation of action/indicates object of desire, like, hate,し(shi) (num) 10^24/septillion/quadrillionていたno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb。(。) Japanese period "."    
kareha muzukashii kao tsukiwoshiteita 。
Grammer form日常会話 (Casual form)Casual form (nichijoukaiwa)
everyday casual language, commonly used between friends and family.
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