Now for the actual story in John 3:1-15 but we'll start with John 3:1-3. We now know that Nicodemus is a Pharisee, about equal to a pro football player in Jewish society. These guys weren't just the priests who knew all about the Old Testament and made sacrifices, they were the big shots for the Jewish people and they hated Jesus because His power and message threatened to take away their "status." John tells us all about how everything that Jesus does has deeper meaning than just the literal definitions. The New Testament relates back to the old showing that centuries before JC, God's plan was in the works and He was giving hints and symbols about what was to come. However, the pharisees didn't exactly look at the Old Testament that way. They preferred to take the more literal interpretation instead of discovering the deeper, richer meaning God also intended. This literal interpretation allowed them to turn the word of God into the Jewish law book and while God did and does want us to follow His commandments, a law book is not what He wrote for us. So here we have Nicodemus, the surface level big shot coming to Jesus by night.
There are a lot of reasons Nicodemus may have chose to come by night (I personally think it was because he didn't want his fellow Pharisees to judge him) but there's also reasons why God planed for Nicodemus to come at night (Nick at Night). Night and day are the same type of opposites a dark and light, night clearly being dark. Dark is used a symbol a lot in the Bible for being lost. Seeing as Nicodemus was lost in the dark, not seeing the light (Jesus) although it was standing right in front of him, we can congratulate God on some more awesome symbolism not only in His word but in real life (because this did actually happen!!!).
Now, although Nick(because that is what we are going to call him now) is lost, he's clearly on his way out because he came to Jesus. But when he got there, instead of asking questions he informed Jesus that "we know you are a teacher come from God, for no one can do these signs that you do unless God is with him." Jesus response to the random comment is even more random, "Truly, truly, I say to you, unless one is born again he cannot see the kingdom of God." To anyone listening (and us reading) this seems to be an extremely odd way to begin a conversation however to Jesus and Nick it wasn't. You see, as we learned in the bridge at the beginning of this post, Jesus knows what's inside all of us. We can pretty well assume that Nick wanted to ask about getting into God's kingdom but felt awkward about asking or Jesus knew Nick better than Nick knew himself and, therefore, told him what Nick needed to hear. Either way, Jesus knew and that's what matters!
John 3:4-7 is some more of the conversation. Nick is confused because when Jesus says "born again" he is thinking of literally crawling back inside his mother (because, as we know, the pharisees are very literal) but that is NOT what Jesus is saying! :) Jesus clarifies by saying that one must be born of water and the Spirit (not that that is much clarification :)). But what I think it is referring to is baptism. No, you don't have to be baptized to be a believer but the water's of baptism are symbolic of the blood of Jesus, it washes you clean. The Spirit is God. When we are born the first time we are flesh or human because we are born from our parents bodies which is flesh. However, when we are washed clean by "water" and the Spirit comes into us making us a new person belonging to another family, we are born again!
Then Jesus shifts the conversation a bit in John 3:8 and starts talking about the wind. He explains to Nick that the wind is like life with God. It is in us and around us, strong and gentle, and altogether beautifully unpredictable. Jesus is telling Nick that their is a new way of connecting with God, a new way of seeing and entering His kingdom. This newness is like the wind and above all else, it will never end!
Now the conversation really shifts directions due to Nick's confusion in John 3:9-13. Nick's confused, Jesus slightly reprimands him and the other Jews for missing the point (and the Messiah). He then makes His point by saying that non of these people on earth have ever been in heaven accept for Himself (Jesus) because He is the Son of Man (God's son in human form come as a sacrifice for us) and came from Heaven. If Jesus is the only one who's been in heaven there is no reason for the people to doubt His word.
Now we get tied back to the OT with John 3:14-15 (last section I promise! :)) To truly understand this we have to read Numbers 21:4-9. (And no, Jesus wasn't being stupid to tell Nick something he wouldn't be able to connect. Remember, Nick was a pharisee one of his job requirements was to know the OT inside and out so he knew exactly what JC was talking about.) So, Israelites complain, God sends snakes, snakes bite, bitten die, people repent, God tells Moses to make a model of the snake so that when people are bitten they look at their death to avoid dying. When Jesus says He will be lifted up like the serpent this can mean his death, resurrection and ascension since all three are part of the recipe eternal life with Him. However, being lifted up onto the cross is what I really see relating back to the snakes in Numbers. We are all sinners many time over and in comparison to God's righteousness we are all nasty criminals who deserve death and hell. Now, before Jesus saved us on the cross, the cross was a symbol of death and evil since it was where the worst criminals died. Since we are all nasty criminals it can also be a symbol of our death. Because Jesus was lifted up onto the cross, those who look at the death and suffering that should be ours will avoid it and be born again instead! (Don't you love how things come full circle.)