It looks like 99% of those prophecies have already been fulfilled during Christ’s first coming. Your best bet is to cite (Mat 24:36) "But of that day and hour no one knows, neither the angels of heaven, nor the Son, 22 but the Father alone.
v39 They did not know until the flood came and carried them all away. So will it be (also) at the coming of the Son of Man.
v42 Therefore, stay awake! For you do not know on which day your Lord will come.
v44 So too, you also must be prepared, for at an hour you do not expect, the Son of Man will come.
Don’t worry about it. Your friend is spinning his wheels. We’ve been in the end times since Chirst’s ascended to heaven. The important thing is to live your faith. If it happens while your still alive you will be ready. If you die before it happens you are still ready.