Question: Why did Samson keep letting himself get tricked by Delilah?
IMO; because God wanted on record the problem of human failure in the face of strong temptation from His main enemy; Satan.
As is shown Samson was a Nazarite; and had taken vows, which he failed to keep (similar to current Israel, see Malachi), but Almighty God enabled him to eventually satisfy his vows, and show the devious Philistines His Great Power in Thousands being destroyed by Samson's last act of Faith.
This story has similarities to Almighty God’s Saving of His people Israel (Ezek. 39:21–29); and the faithful people of the world, in Christ Jesus Messiah!
Some people see Jesus as a latter day Nasserite, and also his place of Birth (Nazareth) indicating such. However, Jesus’ Role is massive by comparison; and His Obedience to His Father will see Millions of people Saved, in the final tally!
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