Coptic Orthodox Diocese of the Southern United States
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If two spiritually, mentally, and emotionally mature young adults are getting to know each other with the intent for marriage, how heavily should each weigh the other's past relationships while deciding whether to move toward a committed relationship. In particular, If the male had impure relationships in the past and has since then undergone penance and repented under the guidance of his spiritual father.  Later he disclosed these past mistakes to a female WITH he is interested in pursuing a relationship in hopes of maintaining transparency between them and a spirit of mutual trust and honesty. The female respects his decision to be honest with her but she has maintained her physical virginity (as well as spiritual) and purposely abstained from physical relations during her college years in hopes of saving her first sexual experience for her future husband. Although the male may attained forgiveness, restoration, a pure heart, and a renewed mind (Romans 12:2), his past mistakes create a hurdle for his future wife because she has to come to grips with his prior shortcomings. There may be a sense of grief on the part of the female because the male is unable to reciprocate a shared initial sexual experience that she rightfully values and has made a conscious effort to preserve and offer for her husband.

In the Litany of the Departed in the Vespers Prayers, the priest prays: "For no one is pure and without blemish even though his life on earth be a single day." If the male in this scenario has offered true repentance and has not returned to commit these sins again, he has been granted grace and forgiveness with a new blank page in his life that began immediately upon receiving absolution.

However, this grace should not be taken for granted. The woman's need to come to grips with her potential husband's past are due to several reasons, including measuring up to her future husband's expectations in comparison to his previous experiences.

She may also be cognizant to the matter that sins in the context of sexuality are difficult to cease because of the obvious pleasure factor that often demands more experiences. Thus, doubt about his character may arise. Is he one that may go in and out of relationships and assume the other person is the problem?

Unfortunately, regarding sins of sexuality, some people insist on repeating the same sin over and over, but choose different partners, different environments, or different circumstances. In addition, if the actual need to commit this specific sin has not been uprooted, the outcome will be the same, and a vicious cycle will prevail.

The problem is not the other person, the environment, or the circumstances, but the person that committed the sin. Thus, true repentance had not really taken place, but only served as a temporary bridge of guilt until the next opportunity presents itself. That is why it is very important that you are honest with yourself first so that you can truly be transparent with her.
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