Now there was a man of the Pharisees named Nicodemus, a leader of the Jews. He came to Jesus at night and said, “Rabbi, we know that You are a teacher who has come from God. For no one could perform the signs You are doing if God were not with him.”

Jesus replied, “Truly, truly, I tell you, no one can see the kingdom of God unless he is born again.”

“How can a man be born when he is old?” Nicodemus asked. “Can he enter his mother’s womb a second time to be born?”

Jesus answered, “Truly, truly, I tell you, no one can enter the kingdom of God unless he is born of water and the Spirit. Flesh is born of flesh, but spirit is born of the Spirit. Do not be amazed that I said, ‘You must be born again.’ The wind blows where it wishes. You hear its sound, but you do not know where it comes from or where it is going. So it is with everyone born of the Spirit.”

John 3:1-8

I suspect if Nicodemus were alive today, we would get along quite well.

His "modus operandi" (well established method of operating) was his logic and rationality. Jesus, met Nicodemus' well intentioned question with the response "no one can see the kingdom of God unless he is born again".

Confused, he asked "how can a man be born when he is old"?

Jesus' response? "Don't be amazed [or confused]" by what I said. He goes on to explain "the wind blows where it wishes. You hear its sound, but you do not know where it comes from or where it is going. So it is with everyone born of the Spirit.

So what does He mean by that?

He's not speaking in some kind of spiritual code. He's explaining the nature of the Holy Spirit using the best analogy at His disposal - the wind.

You can "hear its sound" or see evidence of its presence, "but you don't know where it comes or goes". The activity and presence of the Spirit is very real. But you can't know or discern the details of what He is doing or where He is going. There are details about His activity that are not easy to discern or understand.

Jesus said that "spirit is born of the Spirit". Or our "spirit" must be born of "His Spirit". In other words, the Holy Spirit interacts with our spirit to draw us to Him.

“No one can come to Me unless the Father who sent Me draws him, and I will raise him up at the last day.

John 6:44

There are a million ways in which this can happen.

Paul described the Spirit as "bearing witness with our spirit" (Rom 8:16).

It is this nature of the Holy Spirit that first draws us into a relationship and then enables us to continue to have a relationship with the Father, through the Son, by the Spirit. Jesus sent us the Spirit in lieu of His physical presence.

it is for your benefit that I am going away. Unless I go away, the Advocate will not come to you; but if I go, I will send Him to you.

John 16:7

He [the Spirit] first works with us - drawing us to Him. Then in us - as we mature in our relationship.

And I will ask the Father, and He will give you another Advocate to be with you forever— the Spirit of truth. The world cannot receive Him, because it neither sees Him nor knows Him. But you do know Him, for He abides with you and [then] will be in you.

John 14:17

So, during the process of conversion, something happens. A switch is flipped that causes us to change the way we think. Paul describes it as a renewal of the mind. And note that it's a process that requires some testing or practice on our part.

be transformed by the renewal of your mind, that by testing you may discern what is the will of God, what is good and acceptable and perfect.

Rom 12:2

That's the Holy Spirit in action. Jesus described it as being born again.

John chapters 14 - 17 describe this process in greater detail. The Holy Spirit as Comforter, Helper, and Teacher.

Just one other point about Jesus' statement "no one can enter the kingdom of God unless he is born of water and the Spirit". He could also be referring to our physical birth as an infant ("born of water"), and then the spiritual birth at the resurrection ("and the Spirit"). Both would be a requirement to actually "see" the kingdom of God.