YOU SAID:

My friend has a family, but can't spend enough time with them

INTO JAPANESE

私の友人の家族がそれらと十分な時間を過ごすことができません。

BACK INTO ENGLISH

You can't spend enough time with them in my friend's family.

INTO JAPANESE

あなたは私の友人の家族にそれらと十分な時間を過ごすことができません。

BACK INTO ENGLISH

You can't spend enough time with them to the family of a friend of mine.

INTO JAPANESE

私の友人の家族にそれらと十分な時間を費やすことはできません。

BACK INTO ENGLISH

You can't spend enough time with them to the family of a friend of mine.