Matt and Kailee: Proposing in New Orleans

New Orleans Surprise Proposal Photography

Matt pops the question at Jackson Square with an epic surprise!

When planning on proposing in New Orleans you should be sure of two very important things: 1. that your person wants you to propose and 2. what kind of proposal your person will enjoy. Not everyone would enjoy a big, public proposal. And not everyone in love is ready to take the next step! If you are sure about these two things you are guaranteed to have an excellent proposal.

And Matt? He was certain that Kailee was ready not only to say “yes” but that she’d enjoy a grand gesture. So we got to work!

I will admit, I’d done this type of proposal once before. I generally like to mix it up and try new things. But while this was so much fun the first time, it was not without a few hiccups. I showed Matt the video from the last one and he knew Kailee would love this kind of surprise. It was rapid fast action and heavy on the romance. And it was sure to leave her speechless!

But I didn’t want to make the exact same card again. The handmade proposal cards are a keepsake the proposee can take with them and I want each one to be unique. So I asked Matt how we could make Kailee’s card completely unique. He suggested including their dog, Pretzel, in the card!

As a mother of 4 fur children, I was all for this idea! I had him send me some photos of Pretzel and he asked I make the text in the card “Pretzel gave his blessing. Will you marry me?”

I’ll admit, crafting this card took many hours. I was trying to find a way to cut Pretzel out of the cover but it was proving to be far too difficult. So after many hours in photoshop, I scrapped that idea and went with an artful rendition of Pretzel’s face for inside of the card above the text. It was super cute! I put it inside a red envelope, put her name on the front in gold, and sealed the back with a wax stamp of a heart. This was one part to make the card extra special and one part to make it longer to open so my little petal fairies had the time to work their magic.

We got there early on the day of and it was a good thing we did. Matt could only stall for so long and he and Kailee were already walking towards Jackson Square! We did a couple of rehearsals to make sure we had every step right. I was working with a different team than the first time so all they had to go off of was the video and my instructions. I took what I learned from the last time and made corrections to the action so it would go off even more seamlessly than the first time.

I was a bundle of nerves for this one! I was watching Matt and Kailee like a hawk as they walked towards the spot. I saw him stall on the riverfront for a bit and then start making his way over. But he didn’t walk straight to the spot like I expected! I watched him walk around the side of the platform and was like “oh, okay, he’s going that way”. I alerted my team that it was almost go time.

And then they disappeared!

I was looking all over, admittedly a little bit frantic because I had no idea where they went. Fortunately, they turned up in front of us a minute or so later. Later, Matt would tell me that he was afraid we wouldn’t see him if he came from the side. Little did he know I’d had eyes on him for the last 10 minutes! This ain’t my first rodeo, bb. I got you!

They hit their mark and I gave Vic the signal. I started firing as soon as she approached Kailee with the card. Once the handoff was complete, my petal fairies sprung into action! We didn’t get to rehearse the actual petal dumping for obvious reasons so they didn’t quite make a circle. But it actually ended up looking like a heart instead!

Kailee opened the card, turned to see the petals, and was in obvious shock as Matt took a knee. It was perfect!

These two may have won cutest couple of the year. They were absolutely adorable together! Matt couldn’t stop smiling and Kailee couldn’t stop laughing. They had only been together 10 months but it was clear these two were the real deal.

And apparently the internet has agreed! I posted a reel of their proposal to instagram the next morning. It was my turn to stare slack-jawed in shock when I checked on it an hour later. It had 95k views! And unlike previous popular posts that peter out by the end of the day, the view count has continued to climb for nearly 3 weeks now. At the time of this writing, it has 756k views and 911k likes. Holy smokes! My previous highest view count was 86k. Wild! (update November 15th: it’s got 975k views!!!)

It got so many views on instagram and tiktok that ten days later, after my next proposal in Jackson Square, a woman came up to me after and asked if I was “that proposal chick from tiktok”. On the one hand, it’s cool to be recognized for the work I’ve dedicated my craft to. But on the other hand… uhoh! The last thing I need as a surprise proposal photographer is to lose my anonymity on the street!

I guess I’ll be working in some good disguises from now on. Thank goodness I have a massive costume collection like any good New Orleanian should.

Check out the viral video and a gallery of images from this epic proposal below!

Ready to propose in New Orleans?