John 3:5 English Standard Version (ESV) Jesus answered, “Truly, truly, I say to you, unless one is born of water and the Spirit, he cannot enter the kingdom of God.
The second question could be; “What does it feel like to be born again?”
There is a good reason Jesus compares being quickened in the spirit to birth. It is not an emotional experience. An expectation of a feeling is misleading. It is something that happens to us and not something we control.
As with water birth being born again is a new experience without any true understanding of the kingdom we just entered. What makes it different is the mind that has vivid memories of a past life. Trying to relate kingdom living using those memories will only hinder spiritual growth.
Romans 6:10-12 English Standard Version (ESV)
10 For the death he died he died to sin, once for all, but the life he lives he lives to God. 11 So you also must consider yourselves dead to sin and alive to God in Christ Jesus. 12 Let not sin therefore reign in your mortal body, to make you obey its passions.
The way we lived in sin was by the nature of sin. If we consider ourselves dead to sin, then the way we thought while in sin must not be how we live our lives to God.
Galatians 2:20 English Standard Version (ESV)
20 I have been crucified with Christ. It is no longer I who live, but Christ who lives in me. And the life I now live in the flesh I live by faith in the Son of God, who loved me and gave himself for me.
Allowing Christ to choose the path we walk in kingdom living is not something we instinctively know how to do at new birth, just as a baby cannot walk right after water birth. It is a learned behavior which cannot be learned by the natural mind that is only experienced in walking in sin.
The born again are now qualified to become disciples.