What if repentance is not about feeling guilty, regretful or ashamed? How do you define repentance?

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Didn't Jesus heal on the sabbath? Wasn't that against the Mosaic Law?
Jesus did heal on the Sabbath, which was not against the Mosaic Law

Wasn't it in the Mosaic law that if caught in adultery you had to be stoned to death? Yet Jesus saved a woman who had been caught in the very act of adultery.
The Mosaic Law instructs both of the people accused of committing adultery to be brought before a judge to do a thorough investigation, that the witness are to throw the first stones, and that no one is to be put to death without at least two or three witnesses, so if Jesus had stoned her, then he would have been in violation of the Mosaic Law.

Jesus wasn't teaching those who believe in Him to follow the Mosaic law , but the law of love.
Everything in the Mosaic Law is either in regard to how to love God and our neighbor, which is why Jesus said that those are the greatest two commandments and that all of the other commandments hand on it, so it is the law of love.

" Blotting out the handwriting of ordinances( the law) THAT WAS AGAINST US, and took it OUT OF THE WAY, NAILING IT TO HIS CROSS. Colossians 2:14
The reason why Jesus went to the cross was not in order to free us to become doers of what the Law of Moses reveals to be sin but rather he gave himself to redeem us from all lawlessness and to purify for himself a people of his own possession who are zealous for doing good works (Titus 2:14), so the way to believe in what he accomplished through the cross is by becoming zealous for doing good works in obedience to the Mosaic Law (Acts 21:20). In Matthew 27:37, they nailed a handwritten ordinance to Christ's. cross that announced the charge that was against him, which fits perfectly with the concept of the handwritten ordinance that listed the charges that were against us being nailed to his cross and with him dying in our place in order to pay the penalty for our sins, but has nothing to do with nailing any laws to the cross in order to free us to become doers of what they reveal to be sin.

He already fulfilled the law because we COULDN'T, no one could, because if you broke one it was just like you broke them all. "
According to Galatians 5:14, anyone who has loved heir neighbor has fulfilled the entire law, so it refers to something that countless people have done and should continue to do in perpetuity, not to something unique that only Christ could do. If someone breaks any law, then that simply means that they need to repent and to return to obedience, which is what James was encouraging them to do, but it does not mean that we can't fulfill the law.

For as much as we have heard, that certain which went out from us have troubled you with words, subverting you souls, saying, You must be circumcised (part of the Mosaic law), and keep the law: to whom we gave NO SUCH COMMANDMENT: It seemed good unto us, being assembled with one accord, to send chosen men unto you with our beloved Paul and Silas, men that have hazarded their lives for the name of our Lord Jesus Christ. We have sent therefore Judas and Silas, who shall also tell you the same things by mouth. For it seemed good to the Holy Spirit, and to us, TO LAY NO GREATER BURDEN then these things; That you abstain from meats offered to idols, and from blood, and from things strangled, and from fornication: from which if you keep your selves, you shall do well. Fare you well." Acts 15:24-29.
While it is possible for someone to interpret Acts 15:19-21 as ruling against followers of Christ following over 99% of what he taught, I don't think that it makes much sense to that. It would be contradictory for someone to treat Acts 15:19-21 as being an exhaustive list in order to limit which ways followers of Christ should follow Christ while also treating it as being a non-exhaustive list by taking the position that there are obviously other ways that followers of Christ should follow Christ.

The Apostles didn't even want Gentile believers to be burdened with having to follow the Mosaic Law, but you do.
No, the goal was to avoid overwhelming new believers, which they justified in Acts 15:21 with the expectation that Gentiles would continue to learn about how to obey Moses by hearing him taught every Sabbath in the synagogues, not to reject over 99% of what Christ taught.

You, if you are trying to fulfill the Mosaic law, are saying that what Jesus did, fulfilling the law, wasn't enough and you want to be your own savior. Consider your ways.
Christ fulfilled the Mosaic Law by teaching us how to fulfill it, so there is nothing about us fulfilling it that means that what he did wasn't enough. Jesus saves us from our sin (Matthew 1:21) and it is by the Mosaic Law that we have knowledge of what sin is (Romans 3:20), so Jesus graciously teaching us to experience being a doer of it is intrinsically the way that he is giving us his gift of saving us from not being a doer of it. The reason why God taught His children how to walk in His ways was not in order for us to be our own Savior, but rather that is the way that He is saving us.