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I have made some big mistakes in the past, but I do not know how to bring this up with the guy I am seeing right now, or even if I should. What would you recommend?

Do not feel that you should tell a guy all about your past just because you are in a relationship with him. If the relationship is serious and possibly heading toward marriage, then it is good to be honest with him regarding these issues. However, pray about the timing of this, and do not feel pressured to pour everything out. Be general, and admit that you made some mistakes in past relationships and that you really want this relationship to be pure and focused on God. As time progresses and you feel comfortable and the timing seems right, you may want to disclose more.

If and when this happens, keep the following in mind: Do not be overly explicit in explaining everything that happened. These details could harm the guy you are seeing. Without being in any way dishonest, be prudent about how much you disclose. You might not end up marrying this man, and if you have shared every single memory and hurt, then the emotional bond you have created could make it difficult to break things off.

Also, it would be troubling to know that this man who is not your husband knows things about you that only your husband should know. If you do end up marrying him, reassure him of how much he means to you. A study of 130 couples with strong marriages found that most of the husbands reported that their wives knew how to make them feel good about themselves.[1] Do not talk a lot about how intimate you have been with other men. Simply reaffirm in his heart that he is your man. Frequently the previous intimacies of one spouse will cause feelings of pain, inferiority, or resentment in the other partner. So love him all the more to quell any discomfort he may have about feeling compared to others.

Finally, since you may not have the gift of your virginity left to give him, here is a suggestion. A young woman I know lost her virginity during high school and experienced more than one broken sexual relationship. Instead of giving in to despair that she would have nothing left to give her future husband, she came up with a beautiful idea. She went to confession, made a commitment to reclaim her purity, and wrote a letter of encouragement to herself to stay firm in this resolve. She listed all the reasons she would no longer lead a promiscuous life. She included in this letter all the things she hoped for in a future husband and promised to wait for God to bring them together.

Whenever she felt tempted to return to her former life, she pulled this letter out and reminded herself that true love was possible and that she should save herself for her future husband. Each time she read the letter, she added to it, and she wrote to her future husband. This letter was a constant support for her, and each time she added to it she became stronger in her convictions. By the time of her wedding, she had a large envelope filled with many pages that she waited to give to her husband on their honeymoon.

I know all these details about her, because I am the husband who received those letters. What a comfort and a blessing it was for me to see that, although she made mistakes, she turned her life around and saved herself for me. She could have said, “It’s too late for me. Once your virginity is gone it’s gone. I might as well forget about ever being pure again.” Instead she trusted in the Lord and had faith that he had a plan for her life. Therefore it is never too late. Have courage and trust in God for a godly husband. You are worth it.

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[1]. M. Lasswell and T. Lasswell, Marriage and the Family (Lexington, Mass.: Health, 1982), as reported by Parrott, Saving Your Marriage Before It Starts (Grand Rapids, Mich.: Zondervan Publishing House, 1995), 156.