I have been looking over your site and have been blessed by it very much. I was looking for a question but couldn't find it, so I thought I would ask myself.
I know that going into details about my sinful past with my current girlfriend isn't necessary, but I do feel I should let her know that I don't consider myself to be a virgin. My question is: when should I tell her? We are in a long-distance relationship, and I wonder if I should let her know before I move to her city or after. I know that if it was the other way around, it wouldn't be a deal-breaker for me. But because I'm not 100% sure if that is the case for her, I wonder If I should tell her before we take such a huge step forward, or not (the step being me moving to her city). Should I wait until right before I ask her to marry me (if we get to that), or before I even move to her city?
I am a little scared that I am wanting to tell her to be rid of my own fears of rejection even more than because I want her to know the truth. Also, because I figure if I'm going to get the boot for my past, it should at least be told before making such a huge move. I know this is not acting in faith and not loving without selfishly seeking, so when would it be a wise time to share this be?
When someone has repented of their past, being buried and gone, I typically don't suggest bringing the matter up unless that past can come back to haunt you at a later date. The reason is that bringing up the sins of the past often cause more problems than they solve.
In your case, if you were here talking with me, I would ask if there was a chance of disease or a child appearing on your doorstep fifteen years from now. These sorts of things could impact your future spouse, so she ought to be told what she is getting herself into. Since you feel you need to let her know and that you are certain it will impact your relationship, then I'm not going to argue against saying something.
In regards to when, it should be done before you or she invest yourselves in this relationship. You are planning to move to her city. That is a big change and one you probably would not make if she wasn't a possible wife for you. You are better off knowing now than later. Nor would it be fair if you are set on needing to tell her to wait until just before your engagement. At that point, she would be heavily invested in you emotionally. If she is absolute in wanting to marry a virgin, then the revelation would cause huge problems.
I am assuming that you have not lied to her about your past, just that the topic has not come up in your conversations yet. If I might, you could say something on the order of "Before I come out there, I want you to know that in my past I hadn't always lived as a Christian ought. I've done things that embarrass me now, but I also don't want you thinking I'm someone with a perfect past." That should get the ball rolling.
In discussing these things with her, I want you to avoid getting into details, such as the names of who you were with, how many, or the precise details of what you did. She'll likely want to know out of curiosity, but what will result is an undermining of her confidence in herself and in you. She'll start worrying about how she compares to the girls you've known in the past. You need to assure her that the past is over and done with and that you don't want to relive what you now are ashamed of.
I just wanted to thank you for your timely response. I did speak to my girlfriend about this shortly after your email and after consulting with my pastor. It went very well; it wasn't a non-negotiable for her and she did apologize for not having clarified that my past wasn't something she would hold against me. She did ask questions, and I refrained from details and told her after I answered her second question that I wouldn't answer anymore. She was very grateful that I didn't wait any longer to share this with her also.
So thanks again for the wisdom. God bless you and your ministry.
I'm glad it went well, and thank you for taking the time to let me know how it turned out. I hope you have a wonderful future together.