YOU SAID:

But had Jonh had had had had had had had had had had a better time

INTO JAPANESE

しかし、ジョンはもっと良い時間を過ごしていたはずだった

BACK INTO ENGLISH

But John should have had a better time

INTO JAPANESE

しかし、ジョンはもっと良い時間を過ごすべきだった

BACK INTO ENGLISH

But John should have had a better time