Conversations During Engagement


I am engaged to get married. I love my fiancee, and our relationships is strong, deep, stable, and rooted in Christ. I am excited to marry him! We enjoy each other’s company, rarely have trouble finding something enjoyable to do together, and can simply sit in silence with one another. We can talk about both the good and the bad (hopes, dreams, fears, pornography, etc.).

I have one major source of anxiety or worry, however. I am a virgin, and he is not (this, in and of itself, is not my concern - please keep reading). Together, we will be waiting until we’re married to live together and/or have sex. He is 100% on board with that. I know that he is a different person than he was back when he was in several sexually active relationships, and he regrets many of his past decisions. To be honest, I admire him and am proud of him for the ways that he has allowed God’s grace to transform his life.

Without needing or wanting to know details, there are some questions that I would like to discuss with him regarding his past because I feel as if they will be important moving forward in our relationship. He is willing to answer any questions that I have, but I always feel bad afterwards for asking. Should I feel bad? Is it okay for me to ask personal, sensitive questions like this? Are there any guidelines or principles I should keep in mind when we have discussions like this? I’m not asking for the sake of curiosity - in fact, there are many things I don’t want to know! My motivation for asking is tied to wanting to know him more (since our past definitely plays a role in who we are today) and being able to talk through my fears or insecurities about his sexual past.

I would love any thoughts, guidelines, or advice that you can offer. Thank you!


Like what? You haven’t really given enough information to make an assessment.

What fears and insecurities are those?


Really, what is it you need to know?

What did she look like? Did you love her? Did it mean anything? How long was the relationship? Was she prettier than me? Where, when, who, what, why?

You know all you need to know. None of the things I wrote matter. He already told you he regrets it, and that is all you need to know. You are actually better off not knowing all of the little details, they will only spark more insecurity.

His past is in the past. Let it stay there.


You surely can talk about your fears and your anxieties. If that leads to deeper conversation and questions, it is good. Open, honest communication on your feelings and the reasons for asking questions can allay any concern on either person.


You should have that conversation with him. Not just for you, but for his sake as well. He also needs to know who he is marrying, and what he can expect in the future.


I disagree. Repentant people will still struggle in certain ways, and past sins may carry serious baggage (STDs, pregnancies, arrests, etc). Furthermore, they highlight the patterns of sin that someone may be prone to, and also provide an opportunity to demonstrate how the person has grown and matured since the previous relationship(s). This is need-to-know information for the woman who will be sharing his life, and if she can’t talk honestly to her intended about his past this does not speak well for their future.

Just one example from your list: “How long was the relationship?” A history of a few longterm relationships is rather different than a history of one-night stands, even though both are sinful. And what if he did “love” a previous partner? What’s different about his relationship with his fiancee now? How has his understanding of love matured? What sore spots might he still carry with him?

Now, should she be asking what positions he used with his previous partners, or how many times he did things with them? Uh, probably not; you’re right about the insecurities. And she shouldn’t be grilling him interrogation-style, nor storing up his answers to use as ammunition against him. But I think it very foolish for two people planning to be married not to know about their pasts and their tendencies.


I see your point, but I think maybe it is all in what it is she wants to know. Yes, people have a right to know if someone has a past, has had STDs, things of that sort. But small insignificant details are not important.


I would say that the only things that are important for you to know, now;

Were there any children,whether now living or dead?
The same with former spouses.

You should also be aware of any relationships that lasted more than a year, as there may have been children that he wasn’t told about. But, try not to dwell too much on the mechanics of his sexual past. You know he’s done things that he’s not proud of. Reminding him, imo, can only hurt the marriage.


Do you have any STIs? Did you father any children?

Were any of your partners someone I know well?

That is it. No details. They don’t help either of you.


Yes, I forgot. So many STDs are not completely curable.


I can see asking if he has any STI and if he got tested or checked by the doctor recently. Also if he has any kids from a past relationship.

However, I cannot understand why you didn’t have talks with him to get past your fears or insecurities or whatever before you committed to marry him.
You don’t get engaged to marry somebody if you have a bunch of insecurities about their past relationships or anything else. You’re supposed to be past that and into commitment stage by the time you get the ring and set the wedding date.

Having said that, you either need to ask questions and not feel bad about it, or don’t ask questions. Simple. Make a choice how it’s going to be, then get it all out in the open ONCE and don’t be bringing it up all the time.
We can’t sit here and tell you to feel bad or not feel bad. If the guy is easy to talk to then you should be able to just talk to him without having to have a big discussion with 10 strangers on the internet about it.


This was my husband and me. As someone who hadn’t some of the time I wondered if it was hard sacrifice for him to be without sex. I was his second wife, he was divorced. It really wasn’t. Marriage has times of abstinence/chastity so the time before marriage was not particularly extradordinary.

You don’t know have to know a whole lot. Your are certainly not doing him any favors keeping it all in his thoughts. In my case it would have been more distressing if he didn’t sleep with his first wife. He doesn’t have to regret it. I had him get tested since it really wasn’t a matter of trusting his past I had no idea her past or the past of her first husband, my husband was her second. Not judging her either, not all contact is consensual. Lots of people victims of sexual crimes. I married a man who was married before to a woman who was married before; that is the three people and all their baggage. So testing before. You should know the results so you can do what you need to stay healthy. Most likely he is fine. Your fiancé need not feel guilty. It’s in the past and btw him and the persons and God.

Just enjoy the touch you have before the wedding, cuddles…

Pre Cana class might help with these questions you have for him, we had a number of exercises. Write down the questions and then think if it’s something with long term consequences. Is this really something I need to know or just bring up a memory or pain? Will my knowing benefit me?


The STD’s, “seriousness” of the relationships, and any pregnancies involved would be very important questions as others have indicated. I would add one more…Was pornography use part of his past? Unfortunately, that’s a widespread problem that can be very difficult to overcome and has hurt many marriages. May our Lord and His Blessed Mother help guide you always!


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