What does it mean to be "born again"?

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Judge Hardcastle

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As for Galatians 4, Paul is using an allegory about covenants, not defining Johannine symbolism.
Everybody being baptized in water by John during the time of Nicodemus is turning back in repentance to God according to the covenant of law. There is no unified experience of water baptism and Spirit baptism yet. They are distinct at this time. Only the covenant of law exists at this time. And turning to God according to that covenant bears children who are slaves.

Galatians 4:24
24One covenant is from Mount Sinai and bears children who are to be slaves...

John's water baptism for repentance births sons who have no share in the inheritance. Because the law does not solicit the liberating power of the Holy Spirit (it's not even available to the people of God, yet). Being born of the 'water' of repentance to the law births a natural son still enslaved to the law and the flesh. That's why they have no share in the inheritance. Only sons born according to faith in the promise have a part in the inheritance.

Galatians 4:30
30...the slave woman’s son (the son born of the old covenant of law) will never share in the inheritance with the free woman’s son (the son born as a result of the covenant of faith in the promise).”

That's why Jesus is telling Nicodemus that you must also be born again by the Spirit to see and enter into the kingdom of God. John's baptism for repentance, as necessary as it is, is not good enough. That is Jesus' message to Nicodemus. So fitting to the person he's talking to, and the time of John's baptism he and the people of God live.

John 3:5-6
5...if anyone may not be born of water (John's baptism) and the Spirit (Jesus' baptism), he is not able to enter into the Kingdom of God; 6that which has been born of the flesh is flesh, and that which has been born of the Spirit is spirit.-

John's baptism of water is not enough. You must also be baptized with the baptism that Jesus brings, the baptism of the Spirit. That is the person who will see and enter into the kingdom and reign of God.
 
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Moonwood

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Everybody being baptized in water by John during the time of Nicodemus is turning back in repentance to God according to the covenant of law. There is no unified experience of water baptism and Spirit baptism yet. They are distinct at this time. Only the covenant of law exists at this time. And turning to God according to that covenant bears children who are slaves.

Galatians 4:24
24One covenant is from Mount Sinai and bears children who are to be slaves...

John's water baptism for repentance births sons who have no share in the inheritance. Because the law does not solicit the liberating power of the Holy Spirit (it's not even available to the people of God, yet). Being born of the 'water' of repentance to the law births a natural son still enslaved to the law and the flesh. That's why they have no share in the inheritance. Only sons born according to faith in the promise have a part in the inheritance.

Galatians 4:30
30...the slave woman’s son (the son born of the old covenant of law) will never share in the inheritance with the free woman’s son (the son born as a result of the covenant of faith in the promise).”

That's why Jesus is telling Nicodemus that you must also be born again by the Spirit to see and enter into the kingdom of God. John's baptism for repentance, as necessary as it is, is not good enough. That is Jesus' message to Nicodemus. So fitting to the person he's talking to, and the time of John's baptism he and the people of God live.

John 3:5-6
5...if anyone may not be born of water (John's baptism) and the Spirit (Jesus' baptism), he is not able to enter into the Kingdom of God; 6that which has been born of the flesh is flesh, and that which has been born of the Spirit is spirit.-

John's baptism of water is not enough. You must also be baptized with the baptism that Jesus brings, the baptism of the Spirit. That is the person who will see and enter into the kingdom and reign of God.

I see the framework you’re building, but it depends entirely on importing Paul’s Galatians 4 allegory into John 3. John simply isn’t using covenant‑contrast language here, and Jesus isn’t interpreting John’s baptism. He is correcting Nicodemus’s misunderstanding about birth, not repentance, not covenants, and not slavery vs. inheritance.

In John 3, the categories are the ones Jesus Himself gives:
  • “born of flesh” = natural origin
  • “born of Spirit” = divine origin
That’s why Jesus immediately explains His own terms: “That which is born of flesh is flesh, and that which is born of Spirit is spirit.” He is not contrasting repentance vs. Spirit. He is contrasting natural birth vs. Spirit‑given birth. And Nicodemus confirms the category when he asks, “Can a man enter his mother’s womb a second time?”

And to answer your question directly: in John’s Gospel, “water” consistently signifies the cleansing and renewal God gives when He brings someone into new life. It is the purifying aspect of the Spirit’s work — not a separate action, not a human ritual, and not a physical‑birth category. So no, this is not baptismal regeneration, and Hebrews 10:22 is not defining John 3; it is using priestly imagery. John’s symbolic vocabulary is consistent: “water” always points to divine cleansing and renewal, never to repentance‑effort, covenant‑effort, or physical birth.

If “water” meant repentance or John’s baptism, Jesus’s correction would make no sense. Nicodemus is not confused about repentance; he is confused about birth. Jesus answers the confusion directly by contrasting flesh‑birth with Spirit‑birth.

So the connection between “flesh” and “water and Spirit” is simply this:
  • “flesh” describes the origin of natural life
  • “water and Spirit” describe the origin of supernatural life
John is contrasting origins, not repentance vs. faith, and not baptism vs. Spirit. That’s why “water = repentance” cannot fit the dialogue: Nicodemus’s misunderstanding is about physical birth, not repentance. Jesus’s correction only works if “flesh” refers to natural birth and “water and Spirit” refer to supernatural birth.

Galatians 4 is an allegory about covenants, not a definition of Johannine symbolism. John and Paul agree on the reality of new birth, but they describe it using different categories. John’s vocabulary is σάρξ, ψυχή, and πνεῦμα, and his contrast in John 3 is between natural life and Spirit‑given life, not between repentance and Spirit, and not between law‑sons and promise‑sons.

So while your covenant framework is interesting, it isn’t the framework Jesus uses in His conversation with Nicodemus. I’m simply keeping John’s categories inside John’s Gospel.