How Do You Tell Someone You Are Dating That You Are Not A Virgin?

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Exactly. We “need to get something off our chest” and do that by burdening someone else with it–the spouse or potential spouse. I know of at least one marriage that was destroyed by that. And at least one other that was maintained by not unduly placing one spouse’s burdens of conscience on the spouse instead of the confessor.
First off, the OP regards a potential spouse, or more properly a girlfriend. We no longer discern marriage after we are married. If either of the parties withholds information that can affect marital consent, notably they would not marry this person, chances are the marriage will be declared invalid if challenged.

But we are talking around in circles. I was young and naive and married the wrong person in my first marriage. In the second marriage, I solved that problem by having very specific questions regarding specific issues that would affect my decision in marrying anyone. The choices are to either answer the questions truthfully, lie, or don’t answer them at all. In the first case, I know I married the right person. In the second case, I know that I can get an annulment when I discovered I married a deceitful liar. And in the third case I don’t marry the person.

The OP will have to decide whether to communicate, or not to communicate. The non-communication for me resulted in divorce, The very open communication has so far resulted in a much longer and much happier marriage.
 
Basically, from the variety of different answers I’ve seen I’ve come to one conclusion only- every relationship is different, and there are no set rules for this situation. Therefore, I have decided to just go with the spirit. I will follow the spirit and feel things out with my girlfriend to see how she feels and if it is something she wants to discuss or bring up. At this point, I will answer her questions truthfully, but I see no need of bringing it up. I can see how a woman would not want to discuss such things, but I also see how other women would.

Thank you all for the information

Joshua C.
Something for your consideration. She is a virgin and a practicing Catholic. She knows you are a practicing Catholic. It might be she has never thought to ask you about your past because she assumes, as a practicing catholic, you are like her and have none.

Also, yes, for a woman knowing your mates sexual history is very important. It can literally mean life and death or loss of fertility. There is no way to test a male for HPV. Just because you have been tested for STD’s and are clean doesn’t mean you are actually clean. She has the right to know there is a risk that you could be unknowingly carrying HPV.

In another post you mentioned that it is early in the relationship. In my opinion this is the best time to disclose. If having a sexual past is a deal breaker for her it is better she know now rather than find out later when she is much more emotionally involved.

I agree with everything WarriorMonk has said. This is not just about sexual escapades, its also about knowing you. It’s about knowing where you’re coming from, what experiences you have had that have helped shape you into who you are and about understanding what you have been through emotionally. It’s also about knowing the reasons why you hold the views you hold and why you may react the way you react. Sex is never simple and it’s about a lot more than just sex.
 
The non-communication for me resulted in divorce, The very open communication has so far resulted in a much longer and much happier marriage.
My husband had an extensive sexual history that was based on insecurity, feeling very alone, feeling that sex was the ultimate proof of social acceptance among his peer group and he had some rather hippie “free love” views. Because he was very open and honest I was able to gain a better understanding of his mind than I would have otherwise. We were able to debate and discuss and in doing so further deepen that understanding. If I had married him without knowing what I know I also would misunderstood him in ways that very well may have lead me to jump to the wrong conclusions and those would have lead to divorce. Openness and honesty is why my marriage is successful, too.
 
My husband had an extensive sexual history that was based on insecurity, feeling very alone, feeling that sex was the ultimate proof of social acceptance among his peer group and he had some rather hippie “free love” views. Because he was very open and honest I was able to gain a better understanding of his mind than I would have otherwise. We were able to debate and discuss and in doing so further deepen that understanding. If I had married him without knowing what I know I also would misunderstood him in ways that very well may have lead me to jump to the wrong conclusions and those would have lead to divorce. Openness and honesty is why my marriage is successful, too.
Probably there have been differences at different times. If one studies early English or Renaissance literature, for instance, one is given the definite impression that premarital fornication was very widespread among all classes.

When I was a young man, lo these many years ago, there was a sort of cultural infiltration (“cascade” might be more like it) into the Church following Vatican II. I was in a Catholic college then, and the sexual “liberation” among girls who nevertheless were taught better and turned out to be decent women was simply astonishing. It wasn’t as if they were all inveterate trollops, but it was just sort of assumed that if one went with a girl for a significant period of time and if you liked each other significantly (maybe, maybe “in love”), you were also having sex. It was not uncommon to get the sexual invitation at a rather early point in the relationship. It was a (bogus) part of the “all you need is love” thing that very seriously infected churchmen for a long time. Living together, however, was quite rare.

I’ll admit it was quite confusing if one expected better behavior as the moral norm, and it undoubtedly was harmful in at least some degree. It was particularly troubling when one was going out with more than one girl at the same time. Many is the relationship I ended because of that, not because I thought the girls were tramps or nuts, but because it was “getting ahead of the relationship” and posed, I thought, a severe hazard of their assuming a relationship that actually didn’t exist at that kind of level.

But I do not for a moment doubt that most of them turned to better behavior as they matured. I have kept track of some of the males and females with whom I went to school, and the marriages among them seem no more vulnerable than anyone’s.
 
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