Why I Didn’t Kiss Dating Goodbye // Part II

Last Friday, Chantry drove nine hours to surprise me for Valentine’s weekend. I think it’s safe to say that he’s one of my favorite people, and it’s hard to imagine how I used to manage my life without his daily support and encouragement. Anyhow, over a weekend full of laughter, smiles, and even tears, I was reminded that I’m so very blessed to have such a wonderful, Christian man in my life.

This frame of thought continued throughout most of my week, and I started to think more about relationships in general. Such digressions reminded me that I hadn’t ever written a follow up post for my original Why I Didn’t Kiss Dating Goodbye. Thus, here are some more thoughts on the strict courtship community (made popular books like I Kissed Dating Goodbye and Her Hand in Marriage) in relation to simply having a Christ-centered relationship.


The “you can’t fail” mentality. This is one of the biggest myths ever, because courtship isn’t a fail-safe option to keep heartbreak or temptation out of the equation. To be honest, I’ve seen far more failed courtships than successful ones– mostly due from overly strict and ultra conservative ideas that simply make it far too awkward for young adults to even start a relationship.

On the flip side, it’s also incorrect to say that dating instantly breeds failure of the current relationship or any future relationships. Certainly, if someone is immature about the way they go about dating, then it can cause damage. However, the same goes for any situation that involves humans–we’re prone to make a mess of things no matter what. Thankfully, those who are willing to follow after God’s plan (courtship or dating) can overcome the temptations of the world. 


Always being chaperoned. Yes, because having a dinner date alone is too much sexual temptation. Even when I was pro-courtship and anti-dating, this aspect of courtship bothered me to no end. If courtship is about marriage, then you’re dealing with young adults. Allow the couple to be adults and trust them to follow the path on which they’ve been raised.

Granted, this isn’t saying to throw caution or boundaries to the wind–this is just saying that it’s important to trust young couples (especially if they’re already in their twenties+) to be mature and responsible if they’ve been raised as such. It’s silly to treat couples like children who can’t be trusted, It especially if the plan is to marry. It’s important to let couples in a relationship learn how to stand on their own two feet together.


A near-instant engagement. Courtship instantly places pressure on the relationship, especially since the sole purpose of courtship is marriage. While intentional relationships are a great thing, it’s impossible to tell 110% that you’re going to marry the person you’ve just entered into a courtship with. Instantly placing the emphasis on marriage instead of spending the early stages simply getting to know each other can cause needless stress and unnecessary anxiety.

It’s important to realize that courtship and intentional dating are still very different. When a couple starts courting, conversations of marriage have typically already taken place. Everyone wants to know when the “special day” might be happening. Meanwhile, dating with the intent of getting married is usually handled a bit different. Chantry and I started dating with my parent’s permission, but no one brought up marriage the moment we started dating. Yes, we’ve had plenty of conversations about marriage; however, we’ve brought up these conversations at our own pace. 




Screened communication. This is another popular aspect of courtship that I find excessive, especially since I know many families in the courtship community who insist on partaking and/or screening every conversation between their children. While there is a time for family and a time for counsel, it’s also important to let couples grow closer together without parents filtering each word and every emotion.

If something is amiss in the relationship, it’s certainly important for parents to step in and offer Godly guidance. However, there’s nothing sinful in two people having conversations alone. Take my daily chats with Chantry for an example. We’re honestly pretty un-scandalous: school, work, good morning and goodnight texts, plans for the future… It’s nice to simply share life with someone you love and enjoy each other’s thoughts and words–it’s a beautiful aspect of a relationship.


Courtship is Biblical. With all my studying of the Bible, courtship isn’t mentioned. It isn’t anymore holy  or “Christian” than dating. The important thing to remember is that a strong relationship is focused on God, whether it be arranged marriage, courtship, or dating. The fact that a large majority of courtship followers focus on rules and use God as a way to push their own relationship ideals, traditions, and agendas is really sad.

I’ve seen so many inspiring, Christian couples set beautiful examples of what dating (and courtship!) can look like when done right. Relying on God to strengthen a relationship instead of rules is essential. Rules are mere guidelines that can be broken; however, a relationship built with God as the foundation that comes with eternal and everlasting forgiveness. 

What are your thoughts on courtship and dating?


Chantry drove nine hours to surprise me with these beautiful roses. Seeing him was certainly my favorite surprise, though.

A post shared by Sierra Bailey (@sierrakay_wordsonmypage) on



Chantry drove nine hours to surprise me with these beautiful roses. Seeing him was certainly my favorite surprise, though.

A post shared by Sierra Bailey (@sierrakay_wordsonmypage) on


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