How to say he regrets his having wasted his money. 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自分自分(jibun) (pn,adj-no) myself/yourself/oneself/himself/herself/i/meの(no) (prt) indicates possessive/nominalizes verbs and adjectives/substitutes for "ga" in subordinate phrases/indicates a confident conclusion/ indicates emotional emphasis/indicates question金(kin) (ok) money/metal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,無駄無駄(muda) (adj-na,n) futility/uselessness/pointlessnessに(ni) (prt) indicates such things as location of person or thing, location of short-term action, etc.使ってno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbしまったしまった(shimatta) (int) damn it!/damn!/oops!/oh dear!/oh no!ことこと(koto) (prt) particle indicating a command/particle indicating mild enthusiasm/particle indicating a gentle interrogative/particle used to soften a judgment or conclusion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,後悔後悔(koukai) (n,vs,adj-no) regret/repentanceしたした(shita) (n) did/a past form of the previous verb/tongue/tongue-like object/clapper/talon。(。) Japanese period "."    
kareha jibun no kin wo muda ni tsukatte shimattakotowo koukai shita 。
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when people are being put into a hypnotic state for the first time i often, after placing them in a very light hypnotic state, wake them and ask them to compare their wakening state to that when hypnotised.

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