Roasting the Question: A Series On Dating

A friend of mine recently expressed to me (in mild sarcasm) the hardships that singles have to face during the holiday season, the most prevalent being the onslaught of cutesy, Christmas, couple pictures that begin to fill our media feeds. All too often, the ceremonious stuffing-of-ones-face that takes place on Thanksgiving night is a foreshadowing of what we singles will be doing in solitude all through the cold, cruel months of December through February, while we scroll to reluctantly like your charmingly-filtered pictures, seasons deep in our latest Netflix series to numb the pain, vicariously living through the characters on the screen. Now, before I get messages from the relationally-blessed, this is not a plea to take down your quixotic posts with your stockings. No, I am certainly not an Ebenezer Scrooge. In fact, I feel I am quite the opposite.

This is more-so for all you singles out there (hands up, let’s seem ’em), singles who may be: confused (especially by modern, Christian dating/courtship), burned by relationships (or even by the parents), frustrated with the awkward dance “just friends” has become (where the line is and who even draws it), or are simply hesitant to even step into the dating arena (again or for the first time). 

While my friend and I continued in jest about the single’s struggle, that the holidays somehow unveil an unspoken caste system where couples are higher up the chain than the rest of us misfits, it did get me thinking more deeply about the topic of relationships.

I have had my share of relationships, “flirtships,” friendships, friendzones, drama things, misunderstandings, Facebook-officials, “official-unofficials,” embarrassing moments and the like. When I said who this series is for, I was speaking from personal experience. There were times I did things right, times I thought I knew exactly what I was doing, times I thought I knew “God’s will” and times I had not a clue. The answers I now have are not exactly answers per se, but personal realizations of what I would prefer not to put myself through again. Learning by negation, this method seems to work best for me.

My desire (as with all of my blog) is to share my experiences and thoughts in hopes of helping others. I want to start (or rather, join in on) a conversation that is ongoing. I believe it would help the Christian community a great deal if we participated in the discussion of dating with open ears, if we trusted the Spirit’s leading with our unique relationships more than external pressures and if we became more open and honest about our struggles and desires, our insecurities and fears.

My initial intention for this was a single entry, in which I simply wanted to plug an article about dating which impacted me greatly and changed my mind on a few matters. Yet, as I kept writing, I quickly discovered that there was far too much in my head that I wished to unpack on the subject of dating as the draft rapidly approached 4,000 words, and still was not finished. I found myself stumbling onto topic after topic, scenario after scenario, until, eventually, it became too difficult for me to keep my thoughts linear and contained. One moment, I was enjoying the therapeutic process that writing is…the next, I was grudgingly struggling to organize the term paper I had suddenly manifested. I had spilled some secret ooze locked up in my brain and there was nothing I could do to stop its flow.

I believe this is due to, and representative of, two factors. 1) Not that I have become the love guru, but I have a passion inside of me to help the next generation (or anyone, really) in any way I can, especially when it comes to navigating the relational minefield. 2) We are starving for conversation (or at least I am…or I was, and now I am just reflecting on when I was). There is so much we bottle up inside. We shy from vulnerability. We desire to appear put together, to have answers, to be confident. While these things may give us footing for confidence, in and of themselves, they are not confidence. Confidence is taking a step regardless of having the answers, regardless of being put together. In my mind, the more something pushes us towards vulnerability, the more we bottle up about it. How much more vulnerable of a topic can we approach than that of relationships? It brings out our innermost desires of connection and acceptance as well as our fears of neglect and insecurities all at once.

Let’s talk. Let’s get vulnerable. Let’s get confident, together.


Remember that dating article I mentioned? Well, here it is:

Why Courtship is Fundamentally Flawed” by Thomas Umstattd

Before you turn your nose up at the title, I implore you to give it a read. You would be surprised to know, just as I was, that Thomas was once one of the most pro-courtship individuals you could find. Some followed Paul, others followed Apollos…Thomas followed Joshua Harris (as did I). It may hit home with those who grew up in church culture more, however, there is much insight here for all (parents included). I eagerly share this article because, the more I read it, the more I felt like I was reading my own story…how I wish I knew these things then. It made me realize I was far from alone with the conflict I felt growing up in church culture. If fact, many, many other young people struggle with a lot of the same things I had. At the time, I could not place my finger on exactly what was causing the conflict inside me, but I believe I am a little the wiser now. One of the main reasons I started this series was because of Thomas’ post. In the coming installments of Roasting the Question, I will be referencing it as there are so many parts to it I can relate to and wish to expound upon.

It got so much recognition that he ended up writing a book based off of it (as seen below), per the request of his readers. Only a few chapters in and I am surely captivated. Thomas starts the book with a more in-depth look at his personal story and goes on to address the notion that modern courtship is somehow a more Biblical or traditional approach by covering 4,000 years of courtship’s history and evolution. Interesting stuff!

If you find yourself up for an intriguing read, while I’m piecing together future-posts for this series, head over to Thomas’ blog and check out his article on courtship.

(see book here)

10 thoughts on “Roasting the Question: A Series On Dating

  1. “Confidence is taking a step regardless of having the answers, regardless of being put together.” That sort of sums up how I feel every day. Not having answers, not having it put together, but knowing I must go on. And knowing, that in going on, God will guide and make my path clear, even if it is only one half-step at a time. Looking forward to hearing more, brother.


    1. Thanks for reading.

      And I agree. I really believe that the more I adopt this mentality of progression that my life turns out better in the end. It speeds up processes and builds character, stretches ones trust in God.


  2. I am unsure as to why I am just now getting around to reading your blog. So excuse me while I am extremely delayed and not reacting to your most recent entry. First off, great writing Jonny! I love stumbling across new, intelligent and fresh minded individuals who also are great at writing. Always a treat! Now on to my reaction to the blog entry… I love it. Being one who struggled with the concept of courtship agenda that was so heavily pushed upon me throughout my teen and early 20’s, I really could relate to this article. I constantly fought it, never understanding and able to grasp the benefit of why courtship was viewed as the truest form of “dating”. I was typically viewed (and still today in some circles), as a loose woman who carelessly dated without meaning, when in fact my intentions were pure and simply against the cultural courtship grain that I was surrounded by. I moved away from home at 18 and lived in CO and Austin for years attempting to gain a deeper understanding of myself, the dating world, and who I wanted to be and be with, free from judgemental eyes that I left back home. When I came back to NJ I had thought I had it all figured out and that I could never step in to the courtship world. And then I stepped in to a new church my family had been attending (lets leave it anonymous for the sake of hurting anyone) and again, the courtship world was thrown upon me so heavily that I struggled to stand up for myself. Years later, I am a product and one of the statistics of ‘Courtship divorce’. And I now have a stamp upon my forehead as also being a failure in the church’s eyes the fact that I could not keep my failed and lets face it, abusive marriage together.

    I am only redeemed by grace and grace alone and even married, still struggling but attempting to understand the courtship world better.

    It sounds like you’re on the right track and that you have a solid head upon your shoulders when it comes to this topic, and I applaud you. Stick to your guns, never stop seeking what is best for you, even if it is against the cultural grain you may be up against. Trust me, it will save you from certain heartache and scars that are hard to heal and walk away from in the future. Never stop seeking the truth and plans that God has for you. He works in very mysterious ways!


    1. Oh please you are completely excused! haha. Thank you so much for the read and involvement. I’ve gotten rather lazy but am now motivated to keep writing. I have far too many drafts collecting dust and you are super encouraging. It’s also very nice to know my writing connects to or impacts someone.

      Also, you speak too much truth, why am I the one blogging? Having been around, but not quite in the middle of all of that, I feel a bunch for you and for whatever toxic events that took place around that particular culture.

      And I totally hear you, it’s really hard to stand up for yourself. When you’re surrounded by something and everyone one is advocating it. So so sorry for the troubles you’ve been through. Having sat front row to my sister’s, I can partially understand.

      But praise God for His redemptive ways! And you better believe I’m sticking to my guns now, my walk have never been stronger. I’ve been through enough to know what I don’t want anymore and to share with others what I think is harmful/helpful. Thank you for the many kind words my friend! I look forward to your seasoned perspective on any entries.



  3. I love Courtship in Crisis! Did you know Joshua Harris is doing a documentary called “I Survived I Kissed Dating Goodbye”? I have high hopes for it, but we shall see. 🙂


    1. Ah thank you! I knew someone would realize I slacked off eventually. I’ve recently been encouraged to keep writing this series and you’ve given me yet another reason. It’s sitting in my drafts. I need to do some maintenance on them but I’m actually planning to post on the topic again soon.

      Thanks for the read!


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