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Fill in the blank with the most appropriate option:
If you ______ your money carelessly, you wouldn’t have been penniless in the middle of your holiday.
A) Hadn’t spent
B) Didn’t spend
C) Haven’t spent
D) Wouldn’t spent

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Answer
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Hint: Conditional tenses are used to speculate about what could happen, what might have happened, and what we wish would happen. Many conditional forms are used in sentences that include verbs in one of the past tenses.
There are four main kinds of conditionals:
>The Zero Condition: (if + present simple,….. present simple)
>The First Conditional: (if + present simple, …… will + infinitive)
>The Second Conditional: (if + past simple, ……Would + infinitive)
>The Third Conditional: (if + past perfect,….. would + have + past participle)

Complete answer:
In this question we have to complete our answer in the past form because the sentence is in past tense. So we go to the explanation of all the options that are given.
Option A) Hadn’t spent – is the correct answer because hadn’t spent is in the past perfect form. Hence, it meets the required condition and is the correct answer.
Option B) Didn’t spend – is an incorrect answer because 'didn't spend' is in the simple past form and not the past perfect form. Thus, it does not fit in the sentence. Hence, this is an incorrect answer.
Option C) Haven’t spent - is an incorrect answer because 'haven't spent' is in the present perfect form and not the past perfect form. Thus, it does not fit in the sentence. Hence, this is an incorrect answer.
Option D) Wouldn’t spent - is an incorrect answer because 'wouldn't spent' is in the simple past form and not the past perfect form. It is grammatically incorrect as a past participle (spent) can only be used in perfect tenses. Thus, it does not fit in the sentence. Hence, this is an incorrect answer.

Hence the correct answer is option A i.e “If you hadn’t spent your money carelessly, you wouldn’t have been penniless in the middle of your holiday.”

Note: The given sentence is in the form of the third conditional. The third conditional talks about the past. It is used to describe a situation that didn't happen, and to imagine the result of this situation. Its structure is given below.
                     If + past perfect, would + have + past participle
From the above structure, we can conclude that the answer must have a past perfect form (auxiliary 'had' + past participle).