Question:I have started dating a very godly man. While I am now a devoted Christian who will not get into any physical relationship until marriage, I did have sex in the past. You have no idea how much I regret my past and wish I could undo it but I am only thankful for God's grace and mercy for His forgiveness and love. I am obligated to tell this special man about my past and worried that he'll be disappointed and break up. I guess my questions are: am I obligated to tell him about my promiscuous past even though I am now a changed person? If yes, should I provide the details (how many people I slept with, etc.)?
Your boyfriend likes you for who you are, not who you once were. If you think your relationship is getting serious --that is, you think the possibility of marriage is on the horizon -- then you only owe your boyfriend an explanation for things that might impact your marriage. For example, if you have sexually transmitted disease that could not be cure, he needs to know this before he decides whether to marry you because it is going to have an impact on his life as well as yours. If you suffered damage from a disease, such that you are no longer able to have children, then he needs to know that as well. You should also not mislead him in thinking that he is marrying a virgin, but you do not owe him any details. Just keep it plain an simple, "I wasn't always a Christian and I did things in the past that I'm now ashamed of even thinking about." If your past is going to make you queasy about having sex after your marriage, you should tell him. Beyond that nothing is owed.
Nor should you expect him to ask for details. One of the concepts of Christianity is an understanding of the shame of one's sinful past which has been left behind. "Brethren, if anyone among you wanders from the truth, and someone turns him back, let him know that he who turns a sinner from the error of his way will save a soul from death and cover a multitude of sins" (James 5:19-20). The last phrase doesn't mean we cover up for a sinner who remains in his sins, but that we leave the past of a repentant sinner behind.
If a fact about your past is going to harm your relationship with this man, he isn't worth having as a husband. Consider this, if he is the type of man to hold your past against you, what will happen if accidentally comes up after you are married? How is he going to handle it? Isn't he going to feel that he was unfairly trapped in the relationship? What do you think that will do to the trust between you and your husband?