How I Would Plan My Wedding from Scratch Part II: Starting Fresh + Envisioning My Dream Wedding


March 11, 2024

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I create timeless heirloom paintings for couples looking for an original and intentional way to capture their wedding day, and I do it live.

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Remember back in part 1 where I said the number ONE thing I’d do is hire a wedding planner if I were planning my wedding again (from scratch — thank God I’m not)? I still would. Stand by that hypothetical decision 100%.

Now, we’re a little deeper in the pretend planning process, and I’ve got some big decisions to make. Let’s dive in, shall we?

Defining My Vision

I was PISSED. Like kick down the door, yell my head off, throw a plate kind of mad. Carrie Underwood and Taylor Swift kind of mad.

Why was I so mad?

It’s a long story, and if you don’t end up seething for me, I haven’t done my job to explain just how mad I was…

Buckle in, friend.


I arrive home with my groceries on a Friday night, ready to make my dinner at my house and what do I find? One of my roommates started the self-cleaner on the oven.

Not usually a huge deal, but a big deal when I was about to make my meal that was going to be my dinner.


My sweet boyfriend has a house not far from mine, I haven’t even unloaded my groceries — I’ll just pack it all up and surprise him and SURPRISE — make dinner for him too! He will be thrilled.

I get in my car and mosey over to my boyfriend’s house, not calling before because WHY SHOULD I?!

I pull up and he runs outside…

“You can’t come in.”

I laugh, which upon seeing his face changes to a grimace.

Hubba, what?!

A note here that >>>I don’t get upset. I really don’t. I can let things roll off and “play it cool and dig all jive” (it’s from a poem my dad had me memorize as a kid). It’s just not my way. Never has been…

We could argue suppressed emotions or whatever now that I’m digging deep into mental health, inner child, and all kinds of things with TBM, but overall, I just simply don’t get worked up about many things.

Yeah, so back to that unfortunate event.

I said, “Wait, what?”

Well okay, I thought. That’s weird and very unlike him. But okay — I’m sure I had some choice words to say that might not be newsletter appropriate because, this is real life isn’t it?!

“Yeah, you can’t see inside.”

Weird, but okay? I guess?

So I say, “Okay, well I’ll just run through Taco Bueno for dinner (I am a first year teacher living on a meager teacher salary after all, and I have no extra money since I just spent it on groceries that I couldn’t make dinner with. Ah the irony).

Would you like to have coffee in the morning before I head to my TFA training?”

(at this time ten years ago I was teaching with Teach For America and had training and planning meetings all day Saturday, but I could always make time for coffee with my favorite person.)

“No, I’m having coffee with my mom.”

Okay — you’re having coffee.

With your mom.

Yup, they have a great relationship, but Saturday morning coffee?

I was definitely confused.

He kisses me — “I’ll see you tomorrow for our date night!”

He left me standing there in his driveway with my bag of groceries, and I was left with an overwhelming feeling of confusion and frustration. Little did I know, he was planning a surprise proposal for the next day.

But as I’m writing this (and honey as you’re reading this) what the heck was he thinking?!

I woke up and went into my whole next day thinking this date was going to be one of two things:

  1. A Break-Up
  2. A Marriage Proposal

And after my experience that night, I had no idea which one I was walking into!

But wait… THERE’S MORE!

As I’m sitting on my bed ready for our date night, ready for my boyfriend to come pick me up, he calls me.

“My car is broken down! It won’t start! Can you come over here?”

In my typical let it go like Elsa style brain I was like DUDE YOU HAVE GOT TO BE KIDDING ME.

I’m big on chivalry. Opening doors (which he has ALWAYS done and still does), him doing the driving (part of which is I hate driving at night and always have), and things like that.

This? So out of character.

But his car is broken down, unfortunately.

So I grab my keys, lock up the house, and send up a little prayer that I don’t deck him when I get to his house. (I’m kidding, obviously, mostly.)

So imagine my feelings by the time I get to his house — I’m seething.

I don’t even look, I just get out of the car and slam the door ready for an all out smash down drag out.

But what am I met with?

My boyfriend, standing at the open door, waiting for me with a huge bouquet of flowers.

He’s smiling with a giddy sort of smile, and it’s just enough to kick the anger out of me.

And I knew — this wasn’t a breakup I was walking into.

It was a proposal!

I walk into his house, and it’s covered in flowers and candles. Tons and tons and tons of candles. Like, think Michael Scott’s proposal to Holly in The Office. Which coincidentally is my boyfriend’s favorite tv show.

The table is set beautifully, and the house smells amazing. Oh my gosh the smells.

I’m pretty sure he worked on cooking this meal all day because it was NOT a simple pasta with spaghetti sauce out of the jar or hot dogs.

We’re talking steak, and Parmesan crusted eggplant and tomatoes, a gorgeous salad, (and honestly, more that I can’t even remember because when I think back, I remember the being mad, the candles and the amazing dinner and the proposal).

I stood there and my jaw hit the floor.

He held out my chair, and I sat, still too stunned to speak.

And then, we went through all of dinner and I thought, maybe I’m wrong? Maybe he’s not actually proposing?

He excuses himself to get desert and when I look up again, he’s next to me, on one knee, with the most beautiful ring I could ever imagine. It’s not about the ring, of course, but it was a nice touch (well done, honey!).

I said yes, we called our families (FaceTime was new and not super reliable at this time in 2012) and then we jump in the car to go to The Polo Grill for desert and drinks to celebrate.

And I break down in tears.

Gosh, poor guy I must’ve scared him to death.

As he worriedly asks me what’s wrong, I say that my family didn’t even care that I was engaged! What the heck!?

We’re planning to drive to OKC to see my family, so he says that’s probably when they’ll show their excitement.

I say okay, you’re probably right.

We walk into the restaurant, and the host ushers us through a doorway where I am stunned.

My parents are there! His parents are there! His grandparents! His brothers!

And behind everyone I see my sister, who must’ve flown into Tulsa from Washington DC to surprise me.

Holy crap.

THAT is when I burst into tears.

My twin sister and I were close (twins are as you might guess), but never were closer than when we were both first year teachers trying to figure out what we were doing with only 6 weeks of prior training —

Also visited her ONE WEEK PRIOR in DC… See Above…

we would talk on the phone to each other every morning on the way to school and everyday on the way home. And to this day, we still talk multiple times a day, now through FaceTime, which is much more fun.

It was a great night. A roller coaster of emotions for sure, but I’m so glad I said yes and 12 years later, I’d still say yes every time!

I do feel like I need to explain why he wouldn’t let me come in like he was a little piggy and I was the wolf.

That day, his mom had come by his house to help him get the house ready. He and his mom had decorated everything — and if I came in, it would ruin the surprise. He got the ring in May, asked my dad in June (unbeknownst to me when he went and retrieved my beloved dog Eddy to live with him from my parents house while I was at teacher training.) He had already moved the proposal up from Christmas, to Thanksgiving, to September because he JUST COULDN’T WAIT. I just love him. 😊

And he knew if we went to coffee Saturday morning, he would blurt it out and then the whole surprise would be ruined also.


So, it was a whole unexpected thing — a whirlwind.

This unexpected event was just the beginning of many surprises and emotional rollercoasters that happen when you’re the CEO of your wedding day.

Looking back on my own proposal makes me realize the importance of understanding and communicating what I want for my wedding day. I want a warm and intimate atmosphere, surrounded by my loved ones. I want the aesthetic to be classic and elegant, and my top priority is ensuring everyone feels welcome and cherished.

As I look back on my own engagement, it inspires me to envision the exact atmosphere I want for my wedding day. It’s crucial to be clear about the desired mood, aesthetic, and priorities for the day.

I’m taking time to brainstorm and document key elements that align with my values and aspirations. These elements will serve as the foundation for every decision made throughout the planning process.

In the rest of this post, I will continue on sharing the next steps of my pretend wedding planning journey, diving deeper into the process of working harmoniously with our chosen wedding planner, staying true to our authentic vision amidst constantly changing trends, and building a collaborative relationship with vendors to create a unique, memorable celebration.


Finding the Right Partner: Selecting a Wedding Planner

As the couple (bride), you are the CEO of your wedding. The wedding planner is the person who makes everything happen.

I would research potential wedding planners thoroughly, looking for someone who understands and respects my vision. I would meet with them, gauge our compatibility, and ensure they can provide the level of service I need.

There’s something we need to make note of: full-service versus partial-service planners.

Full-service planners do everything for you. Like literally, everything. Thats why it’s FULL service.

Partial-service planners only does some, and the rest falls on you as the bride or mother of the bride.

I know myself, and I know my life is busy (remember I’m pretending to plan my wedding again in 2024, but when I was engaged I was a busy young Teach For America corps member working my booty off teaching kiddos and coming home to work more (grading, lesson plans, and more) before pulling myself across the floor to brush my teeth and wash my face before I got in bed, only to start the day early again because I arrived at my school no later than 6:15 am daily.

I choose full-service.

And as a bride doing my research, here are the planners I would want to work with. I know I want to have my wedding ceremony at our church (see part 1) and the Plaza of OKC — the Peteoleum Club, so I want a planner who understands that I don’t want a barn wedding, but I love natural elements and want it to feel residential yet still honest to my style. I want it to be unique, but not over the top. (Kind of like my paintings.)

I would inquire with:

Alison Hotchkiss of Alison Events

Annie Brady of Annie Brady Design

Laurie Aron’s of Laurie Arons Events

Merilee Hennings of Ever After Events

Stephanie Marion of With Love, Inc.

I would go into these conversations knowing that not all planners want to plan a ballroom wedding — if you can call it that? Which honestly wasn’t what I saw myself having years ago either, but you can’t beat those GIANT WINDOWS and a beautiful city view.

I want someone who can take my vision and run with it, and make it the absolute best experience for me, my husband, our families, and our guests.


Letting Go of Trends: Staying True to My Vision

The latest TikTok trend is great, but if my wedding is a whole list of trends I will be so unhappy 20 years later when I look at the photos and remember. Coincidentally, I avoided any and all trends the first time around seeing as mason jars and burlap were all the rage in 2013…

I would stay the heck off of social media. My planner is making sure everything is perfect, and there’s no reason to be swayed by what other people are doing. Comparison is the thief of joy, so why compare? It is MY wedding day; and I will do what I want.

As we go through this planning process, it’s important that I trust my planner’s expertise to prioritize authentic moments and our individual style in the design and aesthetic.

One thing I know about wedding planners to be true — they know their stuff. If we let them do their jobs, they will blow it out of the park.


Trusting the Experts: Collaborating with Vendors

Let me tell you, I was once that bride who thought she could do it all. I was convinced that I could single-handedly plan the most epic wedding day and coordinate all vendors.

But, just like that time I tried to bake a 3-tier birthday cake for my baby girl’s first birthday, it was a disaster waiting to happen.

I remember it was the night before the birthday party, and I was still trying to figure out how to make the fondant stick to the cake. I was in over my head, and there was no turning back. I was knee-deep in flour, my kitchen was a war zone, and my stress levels were through the roof.

And guess what?

The cake collapsed.

Elizabeth Zott would be mortified at my lack of competence.

The cake, much like my sanity, was in shambles. My husband ended up making a whole new cake the next day, complete with rosettes in the frosting. Go figure 🤦🏼‍♀️

Looking back, I realize the value of leaving things to the experts. So, when it comes to my wedding vendors, I’ve decided to take a backseat. I’ll acknowledge their expertise and embrace their creative input. I’ll share insights from my past experiences, including the value of vendor recommendations from the planner.

I’ll prioritize vendors who align with my vision, offer personalized solutions, and contribute to the overall ambiance of the wedding.

Because, let’s face it, nobody wants a repeat of the cake incident!

To wrap it up, we’ve taken the first vital steps towards crafting my dream wedding. We’ve dreamt up the perfect atmosphere, hunted down a planner who gets me, placed authenticity at the forefront, and roped in vendors we can trust.


Keep your eyes peeled for my next post where we’ll take a deeper dive into this exciting journey of creating a celebration of love that will leave everyone with unforgettable memories.

And if you’re looking for an unforgettable way to remember your wedding day? Click here and lets chat.

Bringing your wedding day to life, thrilling your guests with a show-stopping live wedding painting experience, and creating a timeless keepsake that honors your sacred bond and will warm your heart every time you look at it – it’s what I do best.

Hey, I'm Courtney.

From behind the easel, I serve timeless brides who still embrace the unexpected by creating heirloom painting experiences that are immersive, one-of-a-kind, and thrilling to watch.

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With a slightly abstract Impressionist live painting experience that captures the love and joy of your story, shows off the beauty of your wedding day, and helps everyone who enters your future home to feel your wedding day, you’ll finally have THE THING that makes your wedding day unforgettable.

And your guests? They'll talk about your wedding forever because of the experience you gave them.


Simply put? This is way more than just a wedding painting.