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But if God exists timelessly,

There is nothing Biblical to support such an answer. It is very consistent theology that God exists like the early church believers believed in time like we do and that our actions are not a reality until they occur. Can God predestine certain events, i.e. like the prophecy of King Cyrus?- yes. But it is consistent with Biblical guide that our choices are not known from eternity past - God talks of evil that never entered His mind, Jesus marveled at a man's faith, God had regrets that he had made man. God knows all that is knowable, but our free will decision to live a life to bless and serve God is exactly that and a decision that God anticipates in real time(Luke 15:10).

I don't believe we can ever "surprise" God - no matter what we do. How would He be able to "work all things to the good of those that love Him and are called according to His purpose" (Romans 8:28), if He doesn't know the end from the beginning? God is omniscient - which means He is all-knowing.

David, in Psalm 139:15-16 says:

My frame was not hidden from You, When I was made in secret, And skillfully wrought in the depths of the earth; Your eyes have seen my unformed substance; And in Your book were all written The days that were ordained for me, When as yet there was not one of them.