How to ruin Your Surprise Proposal
Five simple ways to completely wreck your surprise engagement proposal… and what to do instead.
Nobody wants to ruin their own engagement… right? I would like to think not! But I’ve seen enough people make a total mess of their surprise marriage proposal that it makes me wonder if self-sabotage wasn’t a part of the plan.
Disclaimer: this photo is from a success story!
I’m kidding. Mostly.
I highly doubt any of those proposers were planning to muck things up… they just didn’t know what they were getting themselves into. Most people don’t have any idea how to plan a proposal and, worse, no one to help them sort it out. Sometimes they get lucky and things go smoothly. But other times, they run straight into disaster.
If you’re one of those people, fear not!
My name is Lady and I plan and photograph surprise proposals in New Orleans. I’ve heard the horror stories and I’ve helped people narrowly escape disaster. Instead of yet another post on how to propose in New Orleans, here’s one on how not to. Before you jump into taking a knee, read through these five ways you can mess everything up.
(Disclaimer: The stories you are about to read are true but those photos have not been included to protect the innocent. The photos featured here are all success stories!)
Table of Contents
This one is going to piss some people off (like your future mother-in-law, for example). But inviting your or your partner’s family to your surprise proposal can lead to ruining the surprise or, worse, the moment itself.
A number of years ago, a worked with a man who was from just a few hours outside of New Orleans. His girlfriend was graduating nursing school and he used that as an excuse to bring her to New Orleans to celebrate- and also pop the question.
This guy brought the fam but they knew how to act right!
Since all of their family lived so close, her parents, grandmother, and siblings decided to drive in and surprise the happy couple. I helped coordinate with the family to get them to the spot and out of sight before the couple was set to arrive.
But granny had other plans.
No matter how much the mother-of-the-bride-to-be tried to convince granny they had a strict timeline to adhere to, she insisted on window shopping on Decatur street. It had been years since she’d been to the city and she wanted to visit some of her favorite spots. How do you tell your grandma “this trip isn’t about you!”? You don’t, that’s how.
So while the couple was doing their own pre-proposal shopping per our plan, they ran into her entire family in the Praline Connection. 🤦♀️
This guy included his fiancé’s family because he knew for certain he could count on them.
Mom scrambled to make up an excuse for why they were there- “errr…umm…. surprise! We wanted to take you to a graduation lunch!” But our proposee-to-be wasn’t buying it. And when her partner brought her to Jackson Square, she knew exactly why.
Having the family witness your proposal can be a wonderful thing. But if there’s any chance one of them might go rogue, do not invite them. This could lead to hurt feelings. You can plan a celebratory lunch or dinner with them for afterwards. And if one of the family members would love it if you gave them something to be responsible for- ask them to help you plan the meal and organize the family. You’ll have fewer things to worry about and they’ll feel trusted and included. Win/win.
You ever hear the saying “loose lips sink ships”? Well, my friend, if you’re not careful who you tell about your proposal plans, the good ship secrecy might be going down like the Titanic.
He waited until after the proposal to tell her friends.
Sometimes you need the help of your partner’s friends- they can be useful allies in recon. If you are proposing in your home town or your friends are traveling with you to your destination proposal, they can be super helpful in selling a backstory, too.
But some people just can’t keep their mouths shut... especially once they’re on Bourbon street with a few hand grenades in them. And it’s up to you to know who those people are.
I planned a proposal once for a man who was coming to New Orleans for Jazz Fest with a HUGE group of friends. Something like 12 of them rented out an enormous airbnb for the weekend to not only go to the festival but also celebrate the 30th birthday of two of them- one being the fiancé-to-be. It was a perfect cover. And to get them all to the right spot at the right time, we had one friend pretend to spring a surprise portrait session on the group the day before.
The trouble came later when the group was out on the town.
Not only did he not tell their friends, he flew to a different continent to propose!
You see, our proposer had actually considered the loose lips scenario when he chose to not tell his girlfriend’s BFF of many years. He had planned a proposal once before only to have her let it slip and spoil the surprise. So he knew he couldn’t take that risk again. Even though he knew she might feel a bit left out when it happened without her knowing, he hoped that would go over better than investing so much energy into a proposal and having the surprise ruined again. To make it up to her, he scheduled some alone time for his new fiancé to spend with her BFF that weekend (which came in handy because she was, in fact, not happy about not knowing!)
He had really thought things through. Or so it seemed. What he hadn’t considered was the wild card: alcohol.
Her friends were not only trustworthy but pivotal to his backstory!
Once in New Orleans, the friend group transformed into party monsters. One friend in particular could not handle her booze very well. After one too many shots of fireball she said something along the lines of “I have a present for you tomorrow for after the surprise” to his girlfriend. Naturally, the girlfriend was very curious about this surprise and starting pressing the poor guy for answers.
Things were starting to get a bit heated when the “photo shoot” friend stepped in to save the day. She wasn’t supposed to announce the gifted session until the next day but went ahead and “spilled the beans” in the middle of a loud karaoke bar to take the heat off of our guy.
She sold it perfectly, the secret was safe, and the drunk friend was cut off for the rest of the night.
I can only imagine how it might have gone if she hadn’t been there to save the day!
Choose who you tell very carefully. If there is someone who absolutely needs to know but you cant count on them to keep their lips zipped, wait until the very last possible moment to tell them. I’m talking the morning of the proposal or even a few minutes before. That way they knew ahead of time but they won’t have the chance to mess things up for you.
Look, some of y’all are not as slick as you like to think you are. Or, at least you aren’t as clever as your partners are. But you don’t have to make the sleuthing easy on them!
Now that’s the face of a woman who did not see it coming!
I recently planned an elaborate proposal at a French Quarter Mansion for a couple. We went over all of the ways she might figure it out and came up with excuses for him to tell her if she started asking questions (including a reason for why some keepsakes we were using in the proposal were missing from their house. She noticed! He was ready with an answer. Boom!).
But he made one careless mistake that let her know she was getting engaged in New Orleans: he forgot the receipt from the jewelry store in the car.
She didn’t let on, bless her. But after he popped the question she told him how she knew it was coming. He was a bit crestfallen but ultimately she was happy so it wasn’t too bad.
I can help come up with a million contingencies and backstories for every question they might ask. But I can’t clean up after you! Make sure all evidence of the proposal is well hidden- and that includes covering your digital footprints. Clear search histories, don’t put incriminating meetings on shared calendars, turn off ad targeting, and for the love of Pete, don’t keep the receipts!
A couple of years ago I did the most delightful proposal in front of St. Louis Cathedral. The sun was setting, we surprised her with my signature rose-petal-toss, and they both cried and giggled. It was flawless.
He hired me because he was once the reason his friend’s proposal was not flawless.
I took the lens cap off.
Several years before he planned to propose to hid girlfriend, our guy was asked by his buddy to photograph his proposal. Our guy was an amateur photographer, a hobbyist or enthusiast with a nice camera, not a professional. But his buddy thought that was good enough and didn’t want to spring for a professional.
Our guy had never photographed a proposal before- much less one for his dear friend. He was not only about to watch his good friend get engaged but he was tasked with capturing the moment for prosperity. To say he was nervous would be an understatement.
He showed up early and hid as planned. The couple arrived, his friend proposed, she said yes, and our guy fired off hundreds of shots.
But when he went to look at them on the back of his camera, the were all black. Not underexposed or dark. Just black.
He turned the camera around to see that he hadn’t taken the lens cap off. Not a single photo was taken.
See? I told you so.
This, dear reader, is what I call a “rookie mistake”. And it’s what can happen when you get a rookie to capture one of the most important moments of your life.
Maybe the photos aren’t important to you or your partner. If that’s the case then by all means, get your Uncle Jack with his 25 year old DSLR to photograph it. But if they are, hire a professional who has experience with proposals.
You won’t remember the money you saved ten years from now. You will remember if your photographer completely biffed it.
Of all the ways you can ruin your proposal, this might be the easiest one.
This woman had a solid plan.
Not long ago, I was hired by a guy who wanted me to help him photograph the proposal he planned… on the very next day. The photographer he had hired bailed last minute and he was scrambling to find some help. The worst part- he was already in New Orleans and it was very difficult to get a moment away from his girlfriend to chat.
When he first contacted me, he assured me he already had a plan and just needed a photographer to capture it. So I asked him to send over his plan.
He had planned out a sweet reveal using a beautiful music box he had handmade for her. But he didn’t have anything resembling a plan. The photographer had suggested a busy location in City Park. Not only would his girlfriend would be mortified if he proposed in front of a crowd but there was not enough time for them to get there between their French Quarter dinner reservations and their Downtown Opera tickets. He also had no plan for how to hide the box he made, no ruse to get her to the spot, no backup plan in case it was occupied… nothing.
I was hesitant to even take the booking because I didn’t know how I would be able to save this guy. I told him he would have to make time to talk to me. Even just an hour to slip- maybe away while she was still sleeping or getting ready for the day- would be enough time for me to help him come up with a way to get her to a great location before dinner. He said she takes a long time to get ready in the morning so he’d “go out for pastries” while she showered and give me a call around 9.
This guy had a solid plan.
9 came and went and I was starting to worry about the guy. I wasn’t going to be able to help him if we couldn’t talk through a few key details. When I finally heard from him at 10:30, he was whispering from the bathroom while she was in another part of their suite. 😵💫
He had an idea for a plan and I did my best to help him make it make sense… even though I was really worried about a number of potential plot holes. He assured me it would be fine. It’s hard to take the word of a man hiding in a bathroom but it was either trust he knew his partner or dip. I was starting to understand why the other photographer bailed.
So the plan went he would sneak the box down to reception and I’d pick it up after they left for the day. They would visit a museum and stop in the gift shop on the way out. He’d make a pitstop at a cafe in the park to hit the head before they took a stroll on their way to a fake dinner reservation. I would wait for him at the cafe and hand off the box which he’d hide in the museum gift bag.
I presented potential problems with this plan- what if the gift shop was closed? What if she didn’t want to go in there? What if she wanted to go into the cafe too??? He told me it would all be fine.
He also wanted some decor for the moment so my team and I showed up at the (far more private) spot in the park and I left them there to start setting up while I went to the cafe for the handoff. Our guy showed up, looking flustered and sounding stressed.
This guy had a solid plan.
She hadn’t wanted to go in the gift shop. Her feet hurt from walking around the museum and she just wanted to get back to the car. And since her feet already hurt… she didn’t want to take a stroll through the park.
He left out one important detail when we talked this through, dear readers. They would be in their car. 😮
If driving is an option, we HAVE to work out a contingency for if their partner decides they don’t want to walk. But as already established, he wasn’t big on contingency plans.
I handed off the box, asked him what he planned to do and he said he would park nearby and get her to walk, it would be fine. He managed to fit the music box in his pants pocket (it would no doubt show when he sat down in the car) and said not to worry, he’d get her there.
But worry I did.
This guy definitely had a solid plan.
I headed back to my team who was almost finished setting up. I checked my phone to look for his location and saw a text
“Proposal’s off. I’ll reschedule”
In over a decade and hundreds of proposals this is the first time I had ever experienced someone pulling the plug on their proposal mid-stream. I was kind of dumb-struck…although not entirely surprised.
It was an absolutely stunning day in the park and the setup looked beautiful. But I told the team to go ahead and pack up, the gig was over.
I felt awful for the guy. I knew he had to be heartbroken- and I can only imagine the argument that must have lead to him pulling the plug. But he didn’t have contingencies- even though I told him he really needed to.
I heard from him later that night. He said it was about to turn into a fight so he bailed rather than trying to drag her to a proposal in a bad mood. He said “I should have hired you months ago. I don’t know why I thought I could do this all myself”. 😢
I sure wish he had hired me sooner. He would have had a beautiful proposal- complete with contingency plans and the heartfelt reveal he had dreamed up.
You might think you have everything figured out. You might think proposing is the easiest thing in the world and that you don’t need backup plans. But if some good is to come of this poor guy’s story, let it be that you learn from his mistakes. Shit will happen and you are going to need help.
There are just some of the ways your proposal can fail wherever you plan to get engaged. But when New Orleans enters the chat, you are opening a Pandora’s box of variables you are going to wish you’d been prepared for. Your contingencies will need contingencies and you’ll want a partner in crime who can help you anticipate where things might go sideways.
Don’t wing it. Get New Orleans’ only Proposal Expert on your team and set yourself up for Less Stress and More “Yes!”.
If you think you’re actually ready for this and don’t need any help, I challenge you to try your luck in my New Orleans Proposal Simulator webgame, Proposal Trail.