Summary: When we see that born again is really born from above, Jesus' words make better sense.
The teacher sent from God meets the teacher sent from the Jews
Reading the gospels we are given precious little as to many things Jesus did in His ministry.We have seen Him baptized by John, tempted of the devil and then the choosing of the disciples and the wedding feast of Cana where we are told He performed His first miracle and then He comes to Jerusalem for the Passover and cleanses the temple. So when this Pharisee now comes to Jesus, he says something a bit puzzling.
John 3:1-2 (NASB)
1 Now there was a man of the Pharisees, named Nicodemus, a ruler of the Jews; 2 this man came to Jesus by night and said to Him, "Rabbi, we know that You have come from God as a teacher; for no one can do these signs that You do unless God is with him."
We are told a man of the Pharisees comes to Jesus.
Pharisees were a sect of Judaism that formed during the Macabean period. The Greeks were attempting to force all peoples into the Greek culture. Many Jews embraced this Hellenism, but the more Orthodox rejected it and became so overly legalistic that they formed their own sect called Pharisee meaning “separated ones”
We cannot imagine the obstacle Nicodemus had to over come as a learned old Sanhedrist, to acknowledge a Galilean, un-trained in any schools, as a teacher come from God. While the gospel of John suggests that only Nicodemus came to Jesus that night, it is possible he was not alone.
"Rabbi, “we” know that You have come from God as a teacher….
Who is the “we” here? Perhaps other more Nobel Pharisees came with him and are not mentioned. Perhaps Joseph of Aramathea or Gamaliel. Or perhaps Nicodemus is using the “we” to distinguish himself and others from the main body of Pharisees. It is doubtful that the Sanhedrin as a body thought Jesus a teacher come from God. In fact they accused Jesus of doing what He did by the power of Beelzebub. At any rate Nicodemus comes by night, obviously fearing being seen with Jesus publicly.
for no one can do these signs that You do unless God is with him."
What signs Nicodemus could have known about is unclear since so far Jesus had done just one we are told of.
Jesus has no time for flattery. He knew who He came from and He also knew why He came.
John 3:3 (NASB)
3 Jesus answered and said to him, "Truly, truly, I say to you, unless one is born again he cannot see the kingdom of God."
To the Jewish mind, the Kingdom of God was an earthly kingdom, ruled by a king like David and a time of Wine and rejoicing and wealth similar to the times of Solomon.
I can’t see this kingdom unless what?
John 3:4 (NASB)
4 Nicodemus said* to Him, "How can a man be born when he is old? He cannot enter a second time into his mother's womb and be born, can he?"
Nicodemus’ concern is understandable on the surface. Certainly a man cannot physically be born when he is old and he certainly cannot enter his mothers womb a second time. The physical restrictions aside, what if someone’s mother had already passed away. Would this keep him out of God’s kingdom?