"He used to be a Youtuber who I was good friends with."
Does this mean the person does not do Youtube anymore, and used to be friends with the person who said the thing above, but are not friends anymore? Is there a specific time indicated to when he stopped being good firends with?
Is this the same scenario as:
"He used to be in the military who I was good friends with."
or
"He used to be in the military with me who I was good friends with."
Does this mean the person does not do Youtube anymore, and used to be friends with the person who said the thing above, but are not friends anymore? It is poorly written. The meaning is not clear.
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Does this mean the person does not do Youtube anymore, and used to be friends with the person who said the thing above, but are not friends anymore?
It is poorly written. The meaning is not clear. That makes it hard for me to correct it, since I don't know what it means. It seems that you are trying to pack too much into too few words.