14 Questions I Asked My Fiance Before I Became His Girlfriend

Hello to anyone still following this blog! It feels like AGES since I’ve written here. Every time I begin to write a post, I feel guilty for not doing school, but today I’m pushing the guilt away to write this since this is a question I get asked all the time:

“Grace, I heard you had a list of questions you asked Taylor before you agreed to date him… can you send them to me?”

The answer is always yes! I’ve been so surprised by how many people have asked for my list; it seemed like a small thing when I created it. I was seventeen and had just broken off “talking” to a guy because I had dug a little deeper and found out he was addicted to porn. I was shocked; how did I not see all the red flags? It was like he had wanted to tell me the whole time when confronted. It all came out along with the tears. Later, it hit me, and I had barely asked Mr. Potential Almost-Boyfriend questions that would lead to deeper conversations where I would have been able to at least figure him out by his reactions to my questions.

I started thinking of questions that would lead to deep conversations and would help me get to know the character and personality of any guy I talked to in the future, and I came up with fourteen questions that I wanted to make sure I asked a guy before I agreed to date him.

My questions are blunt and pointed, and HUGE timesavers. They require you to talk about the nitty-gritty, the awkward things that are always in the back of your mind but you hesitate to bring them up, I wanted to make sure my future partner and I were open with each other from the beginning about our pasts, presents, and futures.

Then, I met Taylor and we became friends. Taylor and I talked about everything, and I told him about the list I made to ask guys, he was intrigued and wanted me to ask him my questions just to see. I hesitated.

“They’re super personal and I’m going to ask them to guys who want to date me,” I told him.

“Please ask me.”

I agreed to ask him the less personal ones, stopping at number ten. I was surprised how well it went, each question led to a conversation and more questions that we asked each other, at the end of it I felt like I knew Taylor so much better.

Of course, the inevitable happened, I knew I was beginning to like Taylor, so when he told me that he liked me it was only a matter of time before we were official. Two nights before he asked me to be his girlfriend, I called him because I knew he was about to ask me and I needed to ask him the rest of my questions.

Now we’re engaged, and honestly, I’m not sure how strong (or even existent!) our relationship would be if we hadn’t started on such an open note.

  1. How and when did you become a Christian?
  2. What does being a faithful Christian look like/mean to you? 
  3. What are a four of your priorities in life? 
  4. Ideally, where do you see yourself in five years? 
  5. What are two things about your character that you know you need to work on? 
  6. How do you deal with stress? 
  7. What are you currently studying in the Bible on your own? 
  8. What are four things in your life that you’re the most thankful for?
  9. What are your thoughts on modesty?
  10. What do you do for fun?
  11.   Do you look at porn or have you looked in the past?
  12. How far have you gone sexually?
  13. Why did your past relationships end?
  14.  What are your physical boundaries? / How far is too far? 

I’ve met some people who don’t want to hear the answers to some of these last questions, but it is going to come out sooner or later in some fashion.

I certainly didn’t want to deal with some of these answers for the first time while already heavily invested in a relationship or even married! These questions aren’t to judge your future boyfriend. We all have things in the past we are not proud of and wouldn’t announce to the world. Still, the point is entering into a relationship with transparency or avoiding a relationship that wouldn’t have worked out in the first place. Don’t set yourself up for painful surprises later down the road.

Moral of this post, don’t be afraid to ask awkward questions and have hard conversations! You NEED to be able to have these conversations with your future spouse.

Have you asked these questions? What would you add on this list?

Love y’all!!

-Grace