YOU SAID:

having a friend over and getting sad when they leave made me realize how lonely I was

INTO JAPANESE

友達がいて、彼らが去るときに悲しくなると、私がどれほど孤独であるかを実感しました

BACK INTO ENGLISH

I felt how lonely I was when I was sad when I had friends and they left

INTO JAPANESE

友達がいて、彼らが去ったときに悲しかったとき、私はどれほど孤独だったかを感じました

BACK INTO ENGLISH

I felt how lonely when I had friends and they were sad when they left

INTO JAPANESE

友達ができて寂しくなり、彼らが去ったときは悲しかった

BACK INTO ENGLISH

I missed my friends and they were sad when they left

INTO JAPANESE

友達がいなくて寂しかった

BACK INTO ENGLISH

I missed my friend

INTO JAPANESE

友達がいなくて寂しかった