How to say he had a good time talking with her. 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彼女彼女(kanojo) (pn) she/her/her/girl friend/girlfriend/sweetheartとおしゃべりno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb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,してして(shite) (prt) by/as/indicates patient of a causative expression/acts as a connective/adds emphasis/and then楽し楽し(tanoshi) (adj) fun/excitingい(i) (prt) strengthens a question, assertion, etc.ひとときひととき(hitotoki) (n-t,n-adv) moment/a time/a while/former times/two-hour period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,過ごno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbしたした(shita) (n) did/a past form of the previous verb/tongue/tongue-like object/clapper/talon。(。) Japanese period "."    
kareha kanojo tooshaberiwoshite tanoshi ihitotokiwo sugo shita 。
Grammer form謙譲語 (Humble form)Humble form (kenjougo)
convays a sense of humility, commonly used by store employees, espessially in the service industry.
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Other sentences with translations
tom talked with mary all night.

ask alex.

i waited for ten minutes, though they seemed like 10 hours to me.

though he is young, he never wastes time.

go exercise outside.

this rope is strong, isn't it?

she is in a hurry to see her mother.

he was very fun.

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