A common mistake many German speakers make is confusing when to use 'hadn't' correctly and could form a sentence such as;
The correct sentence should be "You didn't have to stay so late in the office".
Remember,
"hadn't" is only used for negating the Past Perfect. So, "I had been there before" is negated "I hadn't been there before". or "I had had a good time" becomes "I hadn't had a good time".
When we form a negative of the verb "had" in the Past Simple we use "didn't have". So, "I had enough time" becomes "I didn't have enough time", and "I wanted to meet at the office" becomes "I didn't want to meet at the office".
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Excercise: Re-write the following sentences into the correct negative form. The first two have been done for you;
I had missed the train, so arrived at the meeting late. = I hadn't missed the train, so arrived at the meeting on time.
I missed the train. = I didn't miss the train.
I had time to do it yesterday. =____________________
I had looked at his Linkedin profile before I met him. =____________________
We had to stay a long time in the office yesterday. =____________________
I had paid the invoice before they sent the reminder. =____________________
I had a lot of work to do yesterday. =____________________
He thought I had sent the email. =____________________
They had had enough time to complete the project. =____________________
The company had enough staff. =____________________
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Answers:
I had missed the train, so arrived at the meeting late. = I hadn't missed the train, so arrived at the meeting on time.
I missed the train. = I didn't miss the train.
I had time to do it yesterday. = I didn't have time to do it.
I had looked at his Linkedin profile before I met him. = I hadn't looked at his Linkedin Profile before I met him.
We had to stay a long time in the office yesterday. = We didn't have to stay a long time in the office yesterday.
I had paid the invoice before they sent the reminder. = I hadn't paid the invoice before they sent the reminder.
I had a lot of work to do yesterday. = I didn't have a lot of work to do yesterday.
He thought I had sent the email. = He thought I hadn't sent the email.
They had had enough time to complete the project. = They didn't have enough time to complete the project.
The company had enough staff. = The Company didn't have enough staff.