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The Advice Nobody Gave Me When We Got Engaged

Being engaged is an amazing thing, but not everyone's engagement season looks the same. Here's why that's more than okay!
I'm Stephanie May Wilson!

I'm an author and podcaster and my specialty is helping women navigate big decisions, life transitions — creating lives they love.

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The Advice Nobody Gave Me When We Got Engaged

It’s crazy to think about what Carl and I were doing this time last year. We were engaged, just a few months out from our wedding, and we were BUSY. We were registering, figuring out who we could possibly take off our guest list (because we could either invite everyone or pay rent and feed ourselves… you know, options), and ironing out details.

We were on the phone with florists, re-visiting our budget every few minutes, making sure our family and friends had places to sleep, ordering sparklers, and twinkle lights, and bridesmaids gifts online.

We were wedding machines, absolutely.

It’s so interesting to look back on that time. Looking back makes me want to write up a list of advice, of do’s and don’ts for any of you who might be engaged right now.

But instead, there’s something I want to tell you. Any of you sweet friends who are engaged, there’s something I want you to know far more than I want to tell you where we registered, and what we would have done differently, or done all over again.

I want you to know that your engagement season will look different from anyone else’s, and that's okay.

Engagement Comparison

I don’t struggle with comparison as much as I used to, but I have been known to compare my life stages to those around me. I’m looking for benchmarks, for a way to measure if we’re on the right track or not. And so I look at the people who are in a similar life-stage and I compare myself to them.

Am I far enough along in my career? I look at those around me to check. Am I spending enough time with God, or saving enough money, or making smart decisions? I look around to measure.

But I did this more than ever when we were engaged.

The thing is, I’d never been engaged before. So I wanted to make sure to do it right. I was a sponge for wisdom and advice. “Tell me everything!” I pleaded to friends who had gone before.

I was talking about the general things — like who had a good return policy just in case we registered for something we totally didn’t need, and real things — like how much should we be arguing during this season, or how many sessions of pre-marital counseling we should be doing.

I wanted to do it well and so I wanted to learn from those around me. It sounds noble. But what it really was was miserable.

Because the further we got along into our engagement, the more expectations I realized I was carrying. Some friends spent every waking moment together, some friends combined their finances before they got married, some friends fought all the time during their engagement, some didn’t fight at all.

And so with all those expectations (and more and more and more) weighing on me, nothing we did felt right. It all felt like we were messing up in some way, not able to balance in this strange equilibrium between all the relationships around us.

And then came the detour

And then our engagement season got harder. On one day, in one fell swoop, we both got laid off from our jobs. Right in the middle of wedding planning, right after we’d decided to stay put for awhile to create some sort of consistency and safety in our lives, we both lost our jobs. We lost our income, our security, the plan for our lives, and we lost them together.

In that moment, our engagement season veered far off any path we’d been trying to follow. Nobody had told us how to handle this. Nobody had told us what you do when you’re trying to look for jobs, and a city to move to, and trying to find a florist in the city you currently live in, but won't as soon as you get married. Nobody told us how differently we’d react to the news, how I’d need to cry for a good long time, and how Carl would need to start applying for jobs immediately—suddenly terrified that he wouldn’t be able to take care of us.

We weren’t prepared for this. Our friends’ paths no longer helped.

This is not what I wanted for our season of engagement. I wanted it to be all parties and excitement, not fear and loss and grief. I wanted it to be all wedding planning, not job, city, and apartment hunting all at the same time.

I wanted a map — an easy to follow A – Z to show us how to go from dating to married and to do it right.

But all of a sudden we were on our own. It’s as if we were standing in overgrown brush with nothing but a machete, tasked with the job of creating our own path, and our own life, just the two of us.

Carving our own trail

Slowly and totally imperfectly, we did carve our own trail. We figured out how to handle grief together, and how to begin to move on. We figured out how to pick a new city to move to, how to pack up all our things, and to move together. We figured out how to find new jobs, more accurately, how to create our own. We figured out how to wedding plan in the midst of all this, and how to manage our excitement for and our fear about our future all in one heart.

We became a team in those months together—machetes in hand. We learned how to work together, learned what each other needed, learned not how to be a married couple in the generic sense, but learned how to be us—Carl and Stephanie–married.

And I honestly wouldn’t change a thing.

Your engagement will look different, and that’s okay. 

When we’ve successfully completed a season of life, it’s so tempting to want to turn back around and tell all those who follow you what to do and where not to step. And sometimes that’s helpful. But sometimes our advice creates this unnecessary expectation that their lives should look like ours. And that’s just not true.

Your engagement season wont look anything like ours did. Partially because I really hope you don’t lose your jobs in the middle of it, but mostly because you’re not me, and your fiancé isn’t Carl. You are two totally different people in a different place, in a different time, with different circumstances. Sure there are some general points of encouragement we can all toss back and forth. But I can’t tell you what this season should look like, or what it will look like. Nobody else can either.

And so that’s my biggest encouragement for you today as you navigate this crazy, wonderful season of going from dating to married. Do it your way. Carve out your own trail. Nobody else’s path will fit your feet perfectly, and so get ready to blaze a path of your own.

But know that as you do—as you navigate uncharted territory— you’ll grow closer to the man you’re about to marry. You’ll be glad for the road you walked together because it will get you ready for the commitment you're about to make.

Your engagement season will look different from everyone else’s and that’s just perfect.

Can I send you a free download of my book, The Lipstick Gospel? I'd love to! Here's what it's all about: 

Inspired by a broken heart and a wicked hangover, sorority girl Stephanie May Wilson throws in the towel on the life she's been living and packs her bags for a pilgrimage across three continents — determined to find her way again. Exploding preconceived notions that Christianity is for grandmas and girls with ugly shoes, The Lipstick Gospel is the story of how one girl found God in heartbreak, the Sistine Chapel, and the perfect cappuccino.

Click right here to download your free copy!

P.S. My husband Carl and I did a podcast episode all about engagement if you want to check it out here.

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Being engaged is an amazing thing, but not everyone's engagement season looks the same. Here's why that's more than okay!

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  1. Shelly Haney says:

    …and my whole self took a deep breath. Thank you, thank you, thank you for these encourgaging words. 38 days out from our wedding and trying to figure out how to balance college graduation, job search, and getting married is proving to be just as chaotic as I imagined it would be! But it’s words like these that bring me back down to earth and remind me to enjoy the process 🙂

  2. Kristi says:

    The biggest, most intense thank you is owed to you! I have been toying with whether I want to write about my reaction to my engagement and this whole messy engagement season of mine, as a running conversation between my love and I has been him encouraging me that whatever I’m feeling is the way I’m supposed to feel right now. The hardest thing has been trying to figure out if we’re doing it right (or even..right for us) while navigating a long distance engagement paired with immigration paperwork (I’m Canadian moving the USA to be with him). We’ve had to let go of any and all expectations and comparisons, on an almost daily basis…as you can imagine, reading this post came as an incredibly refreshing reminder that we’re doing it the best we can.

    Thanks again for writing this!

  3. Bethany Waddell says:

    As a girl who is getting married in less than 2 months, I needed this.
    I am sure I will look back on this season with a certain affection, but that can be hard to see when I am just ready to be married and not spend every waking moment and every dime earned on a wedding. But I am sure, when it is over, it will have been beautiful, sincere, and worth it! Thanks for more lovely writing, Stephanie…anything marriage-related grabs my attention these days, of course! 🙂

  4. Jamie Jo says:

    I really like your story, and a huge part of me is just breathing a sigh of relief that my engagement period is now over.

    Being only a couple weeks married now, I wanted you to know that your story was encouraging to me when I was in the midst of it. Whenever I got overwhelmed in the commercial chaos of it all, I remembered that others, you and Carl, had to be even stronger during that time of life.

    To those of you who are still in it, the biggest comfort that I had was remembering that there wasn’t a single detail that God hadn’t thought of. So, when I was overwhelmed, searching through Etsy wedding cake toppers, I remembered that God wouldn’t let a single detail fall. He wants to celebrate love even more than I do!!

  5. Kimberly says:

    Ahhhh, this was so encouraging to read. I have been comparing constantly during our season of serious dating and engagement. It’s been so different than what I had pictured it would be. Thank you so, so much for this, Stephanie!

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