Yochanan / John 3:1-4 “Now there was a man of the Perushim (Pharisees) named Naqdimon, a ruler of the Judeans. The same came to him by night, and said to him, "Rabbi, we know that you are a teacher come from God, for no one can do these signs that you do, unless God is with him." Yeshua answered him, "Most certainly, I tell you, unless one is born anew (again), he can’t see the Kingdom of God." Naqdimon said to him, "How can a man be born when he is old? Can he enter a second time into his mother’s womb, and be born?"

Naqdimon was prominent Jewish leader in the time of Mashiach’s first coming; he is mentioned in the book of Yochanan. Naqdimon was a Pharisee, and in the Sanhedrin, (Yochanan 7:50). From his question: "How can a man be born when he is old?", we know that he was already advanced in years, and understood the rabbinical doctrine of ‘born again – born from above’.  He next appears (Yochanan 7:50-51) in the Sanhedrin court offering a word in defence of the accused Galilean; and we may infer from this passage that he embraced the truth of His Messiahship as soon as it was fully made known to him. He is mentioned finally in Yochanan 19:39, where he is shown co-operating with Yosef HaAramati (Joseph of Arimathea) in the burial of Maran Rabbeinu Yeshua HaMashiach.

How can I who am old be born again? Naqdimon answers as if the words of Messiah were only addressed to only him.

The doctrine of being born again was well developed in 1st Century Israel. There were 6 possibilities for a person to be become Born from above / again, BUT not all applied to every man.

1st when a God fearer / proselyte become a convert.
2nd when a person was proclaimed King of Israel.

These it seems do not apply to Naqdimon: There was no indication that he was a gentile who wanted to convert. There is no indication that he was of the line of Judah and he did not ask when will I be King?

3rd when a boy became a man (Bar Mitzvah).
4th when he got married.
5th when he became a rabbi.
6th when he became a Rosh Yeshiva (a Rabbi who is the academic head)

These did apply to Naqdimon: He was Jewish and would have had a Bar Mitzvah. To be a Rabbi and or a member of the Sanhedrin you would have to be married in this period. Since Nicodemus is called teacher he is a rabbi. Since he is called by Maran Yeshua “Are you the teacher of Israel?” it indicates he is a Rosh Yeshiva.

So when Naqdimon was OLD and he had fulfilled all the aspects of the Born from above / again that applied to him, how could he do it again? OR as I (personal) see this conversation, Naqdimon is saying ‘Been there done that, what do you mean Maran Yeshua; is there more? The Hebrew Scriptures says you cannot see the kingdom of God unless you are born from above. This means you enter a new spiritual life through God’s Holy Spirit (because you have placed emunah / trust in King Messiah’s work, and the one who send him, the Holy One of Israel).

To answer Naqdimon’s question Rabbeinu (our Rabbi) Yeshua Melech HaMashiach (King Messiah) used an object lesson with which the aged teacher of Israel was familiar. Just as an uplifted serpent in the days of Moshe became the means for dying Israelites to have new life, so an uplifted Messiah becomes the means whereby men in need of life can look (Zecharya 12:1o speaks of this when people look at the One [Messiah] who was pierced). Allow the words of Scripture to speak for themselves:  "He that believeth on the son hath everlasting life: and he that believeth not the son; shall not see life but the wrath of God abided on him." Yochanan 3:36.  And as Maran Yeshua HaMashiach puts it: Yochanan 5:46 “Moshe wrote about me, and if you had believed Moshe, you would have believed me.” See also Rambam: “anyone who does not believe in Mashiach, or is not anticipating his arrival, he denies not only the later prophets, but also the Torah and Moshe Rabbeinu, because the Torah testifies concerning Mashiach…”

Would you have emunah (faith) in Yeshua Melech HaMashiach and the One who send Him?