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How heavily should a female weigh a male's past mistakes while considering whether to pursue a relationship with him?

This matter should be discussed between the woman and her Father Confessor. Only she can answer this question. If your past makes her that uncomfortable, then she should not continue in this relationship with you toward marriage. It is very hard to build on shaky ground.

If this matter will continue to be a distraction and cause her to question your past and have insecurities about your relationship, these emotions will interfere with establishing a new life for both of you as one.

Thus, the real question is if she can truly forgive you of sins you committed before her involvement with you? If she is willing to accept you as a whole person, past, present, and future, you will have a strong and solid marriage. You must also reciprocate the same sentiment of love and forgiveness.