When do I tell him that I'm barely a virgin?

There's this guy who has become my best friend over the past year and a half. He's a strong Christian and I am, too. We're a year apart and grew up as church kids in the same city until we were school-age kids, and even then I had a big crush on him. He was my first crush, actually.

Even though we live in different states now, we've become extremely close through messaging and video chats and finally got to see each other in person not too long ago. He's an incredible person and we balance each other perfectly. Now that we both know for certain that this will continue and we're going to try to live closer together, I was wondering when would be the best time to tell him a well-kept secret of mine.

When I was 17, I messed around with the only other guy I ever dated. We didn't have sex, but we touched each other, had oral sex, humped, and sent suggestive photos. Even though everything that happened was still my conscious decisions, this guy drug me down to a place I never wanted to go. He pressured me, manipulated me, and threatened to make up lies that he would tell everyone if I didn't go along with what he wanted. I had been such good friends with him that I slowly gave it on multiple occasions. Being with him was the worst year of my entire life.

Now, 4 years later, all the spiritual healing I wanted to receive finally took over, and I was able to forgive myself, forgive the first boyfriend, and return back to mental purity. But now that I've found this "new" guy at 21, along with his humor, charisma, and kindness, I know I'll have to tell him everything that happened at some point in our relationship. This new guy had told me a while ago that all he's ever done is kiss someone. If he and I do end up getting married, I don't think I could go through with foreplay without him knowing I had done it before. Also, he deserves my full honesty before things get very serious.

So what should I do? Should I wait until we've been dating a long time to tell him what happened? Should I tell him after an engagements takes place, or before, in case my mistakes are a deal-breaker for him?

ANY kind of advice would be greatly appreciated. I really need some reassurance in this area. Thanks!

Now this is coming from someone who isn't religious, but I respect that you are and I'm trying to see it from your perspective and go by what you believe in and try my best. What you do now is what matters. You said you have healed spiritually and have forgiven yourself, so it shouldn't matter what you did before. If he loves you, he'll understand, and he should especially since the other guy did such awful things to you. What people do and who they do it with before their current relationship shouldn't matter as long as they weren't hurting anyone. The other guy's next partner SHOULD know all the things he did to you so that she will know what to expect and to now that she probably shouldn't be in that relationship. You didn't do anything to manipulate or hurt someone, so what you did shouldn't matter to future partners. And in a religious mindset, it still shouldn't matter anymore because you've already done what makes you feel makes you right with God. If it makes or breaks your relationship, that's his problem. The person you love and loves you will accept you and love you no matter what your sexual history.

@NocturnalMistress, the only reason we aren't "official" just yet is because he literally lives 800 miles away.

@WaterBaby, whether it came from a religous person or not, what you said was so helpful. I guess I've done the most I can do and the rest will have to be up to him. I'm still wondering about the right time to tell him... but maybe the time will come on its own.

I'm glad I could help. As far as when you should tell him, I would just wait until later in the relationship when physical intimacy becomes more important or if a topic of conversation that it would be relevant to came up. Or just whenever you're ready and it feels necessary.?

While in not-necessarily-religous cases, I would normally say that it really isn't of any importance to tell him. Unless you guys were talking about past sexual relationships one day, you shouldn't feel the need to hide it and be able to feel like you can be completely honest. But if it is really important to you to tell him, then by all means, go for it.

I think the right time will come. If it doesn't, when you get to a proposal, that's the time you should tell everything to each other. If he's a good guy, he will understand. Especially since you didn't even want to do that, but you were emotionally manipulated. It's not your fault.


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