How to Know Whether We Should Get Engaged or Not

Considering these things can help you make a choice that's good for you.
By Reggie Madison
May 10, 2019

Am I ready to be married… to this guy?

Should I take the next step of marriage with her?

Am I sure? Is he ready?

We get along well, but his career isn’t off the ground yet.

She and I have so much fun together. But she isn’t sure if she wants to live in the city or the suburbs.

I believe that I want to spend the rest of my life with him. But the rest of my life may be a long time.

How can I make the perfect decision at the perfect time about the perfect person so that I may have a perfect life?

I get it. Deciding to get engaged or not is huge.

No, it’s not marriage, but it’s a major (and I mean major) step in that direction. Often, there’s a ring, engagement parties, questions about a timeline, etc. The news is blasted on social media. Everyone is celebrating that THE RIGHT PERSON has been found. 

And after all that, other things follow… questions, judgments, self-doubts, uncertainty, and the risk of humiliation and failure.

Questions like, “What if I’m not ready? What if I don’t know my partner well enough? What if there’s still more within me that I need to work out?” 

These are all valid questions! But I’m not sure they’re the only questions you’ll want to be asking.

Approaching engagement and marriage from the perspective of making the right choice RISK-FREE may set you up for disappointment. And trying to check all the boxes on your never-ending personal and relational checklist might leave you marriage-less.

There’s no exhaustive list to foolproof your engagement decision. But as a married man who’s also a premarital education facilitator/coach, I can offer you some things to think about…

Consider these things:

Do you feel genuinely safe with this person?

Can you be your whole emotional, spiritual, psychological, and physical self with them? Are you able to be vulnerable? Or do you hold back because you’re not sure how they’ll react? Does your prospective spouse walk with you through your emotions to help you grow as an individual? Are you a better person because of this relationship?

Is this someone you want to learn how to do life with?

Notice, I didn’t ask if this is someone you can do life with. Is he or she bringing a healthy version of themselves into the relationship? If so, you’re both more likely to learn how to navigate through all life’s ups, downs, successes and failures. You have no idea what the future holds. But while you’re dating, you can see how your prospective spouse handles life’s challenges. Is selfishness an issue? Do you value one another’s thoughts, feelings and wants? How do you handle the unexpected as a couple?

Are we both ready to help one another be our best selves? 

If you’re looking for marriage to complete you, then once again, you’re setting yourself up for disappointment. But if you love this person so much that you want to bring all of yourself into a marriage to love, support, and encourage them, then you may be in a good place. Are you ready for THAT? Are you secure enough to not lose yourself in that journey?

Don’t try to find these answers alone. 

Talk to healthy married couples and close family. Discuss these things with your best friends and with the one you’re thinking about getting engaged to. Don’t necessarily look to them for answers. Instead, let them help you talk through your thoughts, fears, and emotions.

There’s nothing wrong with premarital education BEFORE GETTING ENGAGED. 

I know many who appreciated doing marriage prep before they made a decision. It prevented a lot of embarrassment from calling off an engagement after realizing that this wasn’t the person they wanted to marry. No rule says you can’t have these conversations before getting engaged. And if you have these conversations before you take that next big step, you’re more likely to enjoy the journey and be at peace with your decisions.

Looking for more engagement resources? Click here!

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Build an Unbreakable Marriage Right from the Start! 

(And get a discount* on your marriage license at the same time!)

Preparing for Marriage is an online course that will guide you and your bae on a journey to build a solid foundation for your marriage! From communication to intimacy, conflict to in-laws, we unpack 8 fun and fast-paced lessons in short videos that will provide you with all the essential tools to create a thriving marriage.

Plus you’ll have access to healthy relationship experts, Reggie & Lauren, by email every step of the way to answer any questions or just give you a little encouragement!


*Must live in a qualifying state where a discount is offered on your marriage license for completing premarital education or counseling.

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