Please check my sentences gramatically (7.15)

I hope him to feel better.
I can't imagine him crying.
He is revered as a father figure by our department.
I wish him cheer up as soon as possible.

The biggest sadness is when someone lost their spouse.

He has already used his day off for 3 days.
Company allows 3 day off to employees who their family passed away.
It is essential and needed to employees.

Have you experience to lose your family?

My grandfather's face always portrayed nothing without smile.
One day, I came to leave from the military.

I suggested him to show his smile to me.
It was his first smile that I had never seen.
It was the last moment with him.
I went back to military and I got the news that he passed away in a short time.

I couldn't realize the news because I'd never thought that he would die someday.
I realized his death when I saw his picture in his funeral.

Opening funeral for 3 days is common in korea.
3 day is normal funeral period.

His tomb is located in national cemetery.