No, one may not give the priest permission to break the seal. But you can discuss the matter with him outside of confession, and then he could talk about that conversation.

The seal holds even after the death of the penitent.

First, pointing out the truth is not judgmental. Here are a few more examples of what does not constitute being judgmental:

• It is not judgmental to make a moral appraisal of whether a person’s actions are sinful or whether the person is likely culpable for them.
• It is not judgmental to have a negative emotional reaction to what is objectively evil.
• It is not judgmental to bear in mind that a person you have forgiven has committed harmful actions in the past and may commit them again in the future.

One way to avoid being judgmental is to avoid making rash judgments.

The Catechism of the Catholic Church states:

To avoid rash judgment, everyone should be careful to interpret insofar as possible his neighbor’s thoughts, words, and deeds in a favorable way: "Every good Christian ought to be more ready to give a favorable interpretation to another’s statement than to condemn it. But if he cannot do so, let him ask how the other understands it. And if the latter understands it badly, let the former correct him with love. If that does not suffice, let the Christian try all suitable ways to bring the other to a correct interpretation so that he may be saved" (CCC 2478, cf. St. Ignatius, Spiritual Exercises 22).

Zechariah’s objection was that "I am an old man, and my wife is advanced in years." But as a religiously educated Jew and a priest of the temple, he knew that Abraham and Sarah, the founding patriarch and matriarch of the Jewish people, had been granted a son late in life. By asking for another sign, he demonstrated a lack of faith that God could and would provide.

Mary’s question was entirely different. It implies that she was not expecting to have marital relations with Joseph, because otherwise she would have assumed that the pregnancy would take place within her upcoming marriage, and so she needs information about how it is possible for a woman to have a baby without having had relations with a man. After Gabriel explains that the Holy Spirit would accomplish the task, she accepts without further question.

No, this is definitely not okay. A Catholic cannot validly marry outside the Church without permission (cf. Code of Canon Law 1108), so a civil ceremony and subsequent Church blessing is not a moral option. The Church presumes the first marriage to be valid unless and until proven otherwise through the annulment process, so your friend should not even be dating him.

Consider this scenario: The couple marries civilly and then the Church’s marriage tribunal finds his first marriage to be valid—he doesn’t get the annulment. Your friend will be civilly married to a man whom the Church recognizes is already married to someone else. She’ll actually be living and sleeping with another woman’s husband. She won’t be able to have her marriage blessed in the Church. And, as long as she continues to live as though she’s married to this man, she’ll be barred from receiving the Eucharist and won’t be able to receive absolution through the sacrament of penance. What a mess!

Your friend needs to take a step back and wait for the results of the annulment process. Only then will she know whether this relationship is something she can morally pursue.

Formal canonization is a process that developed hundreds of years after the founding of the Church. Before that, righteous people were "recognized" or "acclaimed" by the Christian communities to be saints. That is why Old and New Testament saints (including the Blessed Virgin Mary) were never formally canonized. Noah is one of the righteous people of the Old Testament who are generally considered to be in heaven. Indeed, in the "hall of fame" chapter of Hebrews, which records the righteous deeds of Old Testament saints, Noah is included in the roster:

By faith Noah, being warned by God concerning events as yet unseen, took heed and constructed an ark for the saving of his household; by this he condemned the world and became an heir of the righteousness which comes by faith (Heb. 11:7).