How to Tell a Date You're Not a Virgin

We were on a road trip when the conversation came up. 

It was about two months into our dating relationship, and we were starting to get more serious. I was driving the car with my boyfriend sitting beside me. The conversation had shifted from casual getting-to-know-you stories about our past, to a brief history of our past dating relationships. Suddenly, I felt myself growing flush. I realized that it might be time to share this regretful part of my past. God had forgiven me, and I had forgiven myself. But...what would my boyfriend think about how I hadn’t saved myself for marriage? 

I pulled the car over to the side of the dusty, country highway. The summer heat beat down through the windshield, making my cheeks even more flushed. “I—have something to tell you,” I stammered shyly. 

Suddenly, my boyfriend put his hand on mine and looked me squarely in the eyes. “I forgive you,” he said. 

My heart stopped. Who was this man, to offer his forgiveness to me? 

Thinking he must be mistaken about what I was going to say, I started to form the words…. “I’ve had se—,” yet before I could even get the sentence out, he repeated his words—"I forgive you.” 

I worried what my future husband might think about my lack of virginity. 

Though I had healed from the damaging effects of this sin, repented and received God’s forgiveness, I also recognized that my past mistake was an offense to my future husband. To not be able to give him the gift of my virginity on our wedding night, to say that he wasn’t my only sexual partner in life—those are heavy burdens. Any chastity talk you’ve ever heard rightfully lays the guilt on thick when it comes to the implications of sex before marriage. 

God knew that what I needed to hear from my future husband one day were the same words that He spoke to me in the confessional years before. And that’s exactly what I was given. Forgiveness...from my then-boyfriend who later became my husband. 

Bringing up your past sexual history to your significant other can be tricky. 

The ‘when’ and ‘how’ of this type of conversation is often one of trepidation for daters. Though everybody’s situation and story are unique, there are a few tips I would like to offer to help you have this discussion with the person you’re dating. 

The ‘When.’

For most people, virginity is not a prerequisite for dating or marriage. Yes, there is sometimes a stigma, especially in the Christian world, about past sins. But in reality, most people make mistakes and do things they regret, especially by the time they reach their 20’s, 30’s or beyond. With that in mind, you do not need to broadcast your previous sexual history on your online dating profile. Or on a first date. Or probably at any point in the early stages of a relationship. 

When mutual trust hasn’t been built up yet, it is really not necessary to have such deep conversations about your past. Assuming that the dating relationship you are currently pursuing holds chastity at the forefront, conversations about anything sexually related are just not appropriate. 

Wait until you reach a level of seriousness in your relationship before bringing up the conversation. By that point, you likely have already uncovered some other skeletons in each others’ closets—annoying habits, flaws, etc. Though sexual promiscuity is not akin to something like nail-biting, it is a part of your history that is better broached in the deeper familiarity phase of a relationship. 

The ‘How.’

There’s definitely no step-by-step guide or rubric when it comes to this type of conversation. However, it is helpful to keep in mind a few basics. 

Healing. Firstly, make sure that you are emotionally prepared to share. You have hopefully brought it to confession, received God’s forgiveness, and found healing for yourself. If you feel that the wound might need some more healing—for instance, if there was trauma or abuse involved—find healing for yourself first before bringing it up to your significant other.

Do not expect them to give you the healing you need. Only God or a professional therapist can do that. (The exception would of course be in something like my story, where God used my future husband to bring that final bit of healing that I didn't even know I still needed.) Ultimately, make sure you are sharing from a place of healing and resoluteness, not from deep woundedness. 

Timing. Be sure to pick a time when you both are focused on the conversation with no interruptions or distractions (a road trip is a great setting for that). You could go into the conversation with the intention of sharing this aspect of your past, or you could wait until the right type of conversation comes up. A good tip is to simply ask the Holy Spirit to guide you in broaching the conversation, and to give you the right words to say. The Holy Spirit always comes when invited! 

Details. You do not need to go into excessive detail in your sharing. In fact, it would not be appropriate, given that you are speaking from a place of healing and repentance. Share only what you need to, from a place of humility and vulnerability. And don’t pry or push your significant other to share about their own potential sexual history until they are ready. 

Letting someone in on your past mistakes is never easy.

Once you share your sexual history with your significant other, this bit of information should not change how they view you. If, for some reason, the person you are dating shames you or thinks less of you because of it, consider it a big red flag. As Catholics, we are called to extend mercy and forgiveness to all, just like the mercy and forgiveness offered to us. If you follow these simple tips on when and how to approach this conversation, the right type of person will receive it with grace and compassion.