How to say i asked her a difficult question. in Japanese

1)私(watashi) (pn,adj-no) i/meは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sigh彼女彼女(kanojo) (pn) she/her/her/girl friend/girlfriend/sweetheartに(ni) (prt) indicates such things as location of person or thing, location of short-term action, etc.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質問質問(shitsumon) (n,vs,adj-no) question/inquiry/enquiry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,したした(shita) (n) did/a past form of the previous verb/tongue/tongue-like object/clapper/talon。(。) Japanese period "."    
watashi ha kanojo ni muzukashii shitsumon woshita 。
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