Virgin dating a non-virgin. How do I deal with it?

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To respond to your analogy regarding bad credit / bankruptcy, it would be much more of a red flag to me if someone had declared bankruptcy than if they were not a virgin.
Which, I think, is probably not an uncommon view, but also an indication of why the state of both chastity and of marriage has fallen so low in the current culture. EasterJoy’s analogy seemed quite striking and apt to me.
 
I can relate to this story on many levels, though my situation is a bit different.

I have been married for two whole whopping months now. Like you, I was a virgin when I married. I met my wife at a Catholic young adult group and we had talked a lot before I asked her out on a date. We fell for each other very quickly. We were both strong practicing Catholics and prayed together and regularly reaffirmed boundaries with each other and committed to chastity.

There was a time about a month after we became boyfriend/girlfriend that she had a talk with me about her past. She was very nervous because she was afraid it would change things between us. She told me about the last relationship that she had before me. Even in her teens, she was in youth group and wanted to be a good Catholic and live a chaste life, etc. But she had a boyfriend who was a bit older than her (she was in her late teens, he was in his early 20s) and he was not a good person, very bad influence. She told him that she wanted to wait until marriage for sex, and he continually pressured her and she continually resisted. He and his friends were borderline alcoholics and one day she was over at his apartment and he got really drunk and then raped her. After that happened, since she had lost her virginity her resolve to remain chaste was somewhat broken and sex became a regular part of their relationship She said that she went through all kinds of rationalization for why she stayed with him, but after two years of living in a verbally, emotionally (and sometimes physically) abusive, unchaste relationship she finally decided that she was not living the life she wanted to be living, that she was not being true to herself or her faith, and she broke up with him, tearfully went to confession and resolved to live her life for Christ, then experienced a deep interior conversion. She said it was like a huge burden was being lifted from her shoulders or being released from prison. She was able to finally be herself again and live her faith like she wanted to and make the right decisions. It was two years before she dated anyone, as you can imagine she was pretty wary about relationships after that one.

Well needless to say I was a bit shocked by much of her story. I remember thinking over it for a few minutes and then deciding that this should in no way impact our moving forward. I believed then as I do now that God has the power to change hearts and heal wounds. Our relationship definitely felt different after that; I guess the more you learn about a person, you begin to see them differently, and to learn that much all at once can be a bit of a shock to your system. I struggled with hating her ex boyfriend for a while (even though I never met him) and this became a little more of a challenge after I moved because it turns out that my former roommates that I moved in with lived in the same neighborhood that her ex-boyfriend used to live, and the first day she drove out to see me she realized this, and drove past the apartment where he used to live. It was hard for her too, because of the negative memories associated with that place. But those negative feelings faded and we both moved on.

I am saying all of this to tell you that you should believe in the power of the gospel to change hearts, minds and lives. If your boyfriend is regularly pressuring you then yeah that would be good a reason to break up (Also you should both be regularly reaffirming your boundaries). But if you are just dealing with negative feelings about his past… Frankly I would say get over them. They’re not worth breaking up with someone over, especially if he is really that great of a man. The feelings won’t last forever, and if you do end up getting married, I will tell you that you won’t think of his past again. The past is the past.
 
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