notadictionary.com
なんか娘が難しい顔してるから、どした？って聞いたら…
→ “I asked, 'Something's up? You've got a serious look on your face,' because...”
なんか nan ka = something / somehow (adverbial filler)
娘 musume = daughter / girl (noun)
が ga = (subject marker particle)
難しい muzukashii = difficult / hard / serious (i-adjective)
難 mu = difficulty
しい shii = adjectival suffix indicating state
顔 kao = face (noun)
してる shiteru = doing / having (colloquial contraction of suru + te iru)
し shi = do
てる teru = present continuous aspect marker
から kara = because / since (conjunction)
、 = comma (punctuation)
どした？ doshita? = what's wrong? / what happened? (colloquial contraction of dō shita no?)
ど do = how / what
した shita = did / past tense of suru
って tte = quote marker / colloquial 'to say' (particle)
聞いたら kiitara = when I asked / if I asked (conditional form of kiku)
聞 ki = hear / ask
いたら itara = if...then / when...
… = ellipsis (indicates trailing off or suspense)
