When Do You Know You’re Ready to Pop “The Question?”

Kevin and Elynn Engagement (26 of 61).jpg


It’s been 5 years.


Yesterday marked 5 years since we decided to journey together as a couple.



And on December 29th of 2015, after much deliberation, anxiety, reflection, and anxiety (did I mention anxiety?) I finally decided to pop the question:

“Elynn Rodriguez, will you marry me?”

Watch the proposal video here! 

As a note to myself, and to others who might benefit from this, I decided to write what I wish someone would have told me a few years ago.

Here are 5 principles that guided me towards taking the next step in our relationship! 

And she agrees with them 🙂

1) You know your “why.”

Your “why” is essentially your purpose statement – the reason you exist in this world. The process of formulating your “why” statement begins with an exploration of the following: a) who you are and b) what you want to do in this world.

Your “why” gives you purpose and clarity to everything you do. Once you are clear on what you are here to do, you will then be able to distill all areas of your life and determine if something, or someone, is worth pursuing.

This is crucial. Because till you know who you are, you will be incapable of truly serving someone else.

Service is important since it’s the bedrock of any lasting relationship, especially if you’re planning to put up with each others’ nonsense for an extended period of time.

2) You’ve had meaningful conversations with your significant other.

If the first point deals with the “why”, this point deals with the “how.”

The pre-engagement phase, or the dating phase, of any relationship is probably the best time to discuss important questions, especially pertaining to the future of your relationship.

We’d even argue that this should be your primary focal point of your dating phase as your relationship gets more serious.

The more questions you discuss with each other, the more meaningful conversations you will have. The more meaningful conversations you have, the more clarity you will have about the future of your relationship.

3) You’ve had meaningful conversations with trusted people.

The phrase “Love is blind” may actually have some truth in it. For how you perceive each other in the relationship may affect objectivity in important decision-making.

If you’re like us, you’d benefit from the counsel of trusted friends and family. They can identify potential “blind-spots” that you might have missed and may be able to give you much needed advice on whether you should continue or not.

While others’ opinions shouldn’t be the sole determinant of your relationship, they should not be entirely discounted, especially if you know that they have your good in mind.

4) You know that he/she is willing to journey with you.

We believe that two people can have different pursuits in what they want to achieve in this life and still thrive as a couple.

However, multiple pursuits without a single commitment to journey together will inevitably cause heartache, frustration, and pain.

Elynn and I are both very driven. Both of us have our own dreams and aspirations. After multiple conversations, we realized that if we don’t commit to appreciate and affirm each other on our individual pursuits, we will be end up being roommates and not a team.

We knew that after we learned to appreciate each others’ pursuits, after we revisited and revised our plans in light of a potential marriage, and chose to journey together, we felt somewhat ready to take our relationship to the next level.

The biggest myth is that you have to have everything figured out before popping the question. Do figure out as much as you can. Plan as much as you can. But know that you can never plan enough.

What you need to know at this point is that he/she is willing to stick it out with you as a teammate as you figure things out together.

5) You know you’re making him/her better.

If you’re not in the relationship to make them better, you are in it for self-serving reasons. You’re either growing together, or not growing at all. There’s no middle ground.

Marriage, from what I hear, transforms people. The more life is shared between two people, the more they begin to reflect and complement each other in unmistakable ways.

We had to know if our relationship was actually making us better individuals well before considering the question of marriage.

If we were not already making each other better and bringing the best of each other in our relationship, marrying each other would be the quickest way to a collectively miserable life.

Take some time to do some honest self-reflection with the following questions: “am I making him/her a better individual?” and “is he/she making me a better individual?” 


At the end of the day, relationships can be messy, wonderful, revealing, and inspiring. Choosing to commit to a relationship for life is one of the most important decisions you can make! 

A decision worth making is a decision worth thinking about, and these 5 principles helped us think better about the decision of a lifetime.

What about you? If you’re engaged or married, what would you add to this list? If you’re not, what do you think about this list? Leave a comment below!

Published by Kevin Wilson

Third-Culture Kid. Millenial. Christian. Seventh-Day Adventist. More about me on the ABOUT page! Check it out!

2 thoughts on “When Do You Know You’re Ready to Pop “The Question?”

  1. Good thoughts Kevin! 🙂 Im reading Sacred Marriage by Gary Thomas and it’s a pretty good read if you haven’t already read it!

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