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A few months ago, my soon-to-be brother-in-law, Ryan, gave me a call I’ve been waiting for. He wanted to know how to plan an epic surprise proposal all without my sister suspecting a thing. couple of weeks ago, I helped my soon-to-be brother-in-law pull off this insane surprise proposal, all without my sister suspecting a thing. You might recognize these two from their “Not Engagement Photos” session a few years ago, so this has been a long time coming. Girlfriend thought every day was going to be THE day, so we had to plan like no tomorrow to make this work. I’ve got that story and all the deets on how to pull off an epic surprise proposal below, so strap in because this is a good one.
If you’re anything like my bonus-brother Ryan, you’ve known for quite some time that you’re ready to make it official and plan an epic surprise proposal to your partner. SO exciting! Hang tight, though! There are some big decisions to make.
If you’re going to propose with a ring, this is where you’ll start the planning process. No matter what ring style you go with, you’ll need some lead time for it to be ready to pop the question. If the ring is custom (most end up being at least semi-custom) you’ll want to put aside at least 8 weeks for the ring to be made and ready to go. Talk to your jeweler about times, but this will determine when you’ll actually have a ring in hand so you can finally propose!
Before we talk about location, I’m going to tell you what I told Ryan and every other couple I work with. When it comes to location, you can pick 2 out of these three elements:
Think about what’s most important to you and your partner. For Ryan & Devyn, privacy was the number one priority. Having discussed their dream engagement years ago, they both agreed that a big crowd of people cheering and looking on would make them uncomfortable. They wanted this moment to be just for them, but Ryan also wanted an absolutely killer view. This meant that Ryan would have to be okay with the location being hard to access, which he was totally game for!
Since most couples hiring a photographer are looking for that killer location with a gorgeous view, that means you’ll have to compromise on either privacy or access, so pick which one means more to you, and you’ll have a much easier time choosing a location.
For Ryan’s proposal, this meant he had to rent a Jeep to get up a rough, high-clearance 4×4 road.
Once you’ve nailed down your location, you can start talking with your photographer about dates and availability so you can make this thing happen!
Hot tip: if you start talking to a photographer early in the planning process, they’ll probably have some sweet locations in mind you may not have considered.
Who do you want to be there when you propose? Some couples want to start celebrating right away with all their people by their side, and some want total privacy. If you want to include your dog(s), do it! You need to (at least loosely) make this decision early, because more people usually means more things to coordinate and keep secret. Like I said earlier, these two wanted total privacy (plus their pup) so it ended up just being the five of us there.
Are there any extra details you or your partner want to include? For example, Devyn said in passing several times that she wanted to be dressed nice and wearing makeup if there were going to be photos taken, so we needed to incorporate that into our plans. She also wanted to be totally surprised. Does your partner want their nails done? Do you want them to be shocked, or do you want it to be a drawn-out day of love and surprises? Write down any other special requests the two of you have, because now it’s time to create your cover story.
Knowing that Ryan wanted privacy, an epic view, everyone looking cute, their pup, photos, AND knock-her-socks-off level surprise, we had quite the story to come up with. I mean, figuring how to plan an epic surprise proposal is not an easy request when you have someone who knows a proposal is somewhere on the horizon. How do you get a VERY smart & suspicious girl into the middle-of-nowhere looking photo ready without rising any suspicion? You lie. You lie a lot, and you tell convincing lies.
Here’s our tangled web:
Two weeks before the proposal, I called Devyn asking for a big favor. I told her that I’d just booked a last-minute off-roading elopement in Sedona. I told her that my husband, Ty, had initially agreed to tag along as driver since he’s better at off-road driving than I am, and I wasn’t comfortable driving up the road by myself. The problem was that he couldn’t come along anymore. He had to fit in one last hike before embarking on his Rim to Rim hike in the Grand Canyon the following weekend.
In my best “please help me” voice, I asked if she’d be willing to tag along with me while I drive this road as my emotional-support-human, and she said yes! I told her we’d make a weekend out of it since the elopement was only 4 hours on Sunday morning, and she was stoked.
Once she was on-board with that, I started to let her on on the other bits of the plan.
I told her the couple was from Flagstaff, super chill, but that we hadn’t met yet, so they wanted to grab drinks with us after they checked into their hotel. They were going to stay at L’Auberge, one of the nicest resorts in Sedona, so we needed to look nice. The plan was to pick her up in Phoenix, get into Sedona, check into our hotel, grab some lunch, get ready and do our hair/ makeup, and then snag drinks with the couple. After that, we were going to do a quick scouting trip to the location so I could “practice the drive one more time” and make sure the location was all set. After that, we’d grab some real dinner, go to sleep, and be ready for an early morning elopement!
There, of course, was no elopement. We just needed to get our girl to Sedona.
On Saturday morning, Ty and I drove up to Phoenix with two bags of camera gear– the real bag that Ty would take with him, and the fake one I had to take to keep up with my story. When we got into phoenix, we stopped at a Starbucks and picked up coffee for everyone. I dropped of Ty, the real camera gear, and his overnight bag inside to be picked up by Ryan later and headed to their apartment by myself so she’d be none the wiser.
Ten minutes after Devyn and I hit the road, Ryan quickly packed his bag, hopped in his car, and picked up Ty at the Starbucks. (Ryan deactivated find-my-friends two days before and blamed it not working on a software update, so she couldn’t see where he was).
While Devyn and I got checked into our hotel and grabbed some lunch, the boys were busy checking into Devyn & Ryan’s real hotel room and picking up the rental Jeep.
After we ate (I only choked down three bites of salad I was so nervous) Devyn and I got dressed and ready for drinks. I told her we needed to be at L’Auberge by 4:00, so we were in the car fighting Sedona traffic by 3:30. Meanwhile, the boys had picked up the Jeep, and I received the code “we’re on our way up” text right on time. We planned ahead of time for Ty to text me “You girlies having fun?” which was the code for them starting to head up the trail, which they did right at 3:30 to give them a good head start. They needed to be in place with ample time, so we didn’t catch up to them before they were ready.
About 2 miles from the trailhead/ L’Auberge, at exactly 3:55 PM, I received a text from the “bride.” She said “Hey, I tried calling, but it went straight to voicemail. We just realized that “groom” forgot his shoes in Flag. It’s about 2 hours round trip for us to go grab them, so can we postpone drinks until then?” Pretending to be confused, I showed Devyn the text, and called the “bride” back. My good friend, Kaitlin, was a great sport and played the part of mildly distressed bride beautifully. We agreed that we’d just flip our plans around and scout/ practice driving first and meet for drinks second when the couple were back from Flag.
We had to do it this way for a couple of reasons:
Once we got off the phone and I was done feigning confusion, we took the very next turn and headed up the trail in full hair, makeup. dresses and heels. It was a bumpy ride, but we made it safe and sound. We parked the car, and I “accidentally” laid on the horn to signal the boys that we were coming. I told Devyn that one of the rock formations had potentially fallen, but that I wanted to check for myself to see if the area was still usable. We passed the first and second outcroppings of rocks, and then I spied Ryan through the trees.
“These all look great.” she said as she peered around each corner. I scooted ahead of her and pointed her toward the final outcropping where Ryan stood. “Here it is.” I said. “This one’s gorgeous.”
When she came around the corner and saw Ryan and their Golden Retreiver, Fitzgerald standing there waiting, her jaw nearly hit the floor. Through shocked tears, all she could say was “what are you doing here?”
While she got her bearings and Ryan tied Fitz to a tree, Ty came out from his hiding spot in the trees and handed me my camera. I ran to the closest rock outcropping and Ty and I photographed one of the most magical proposals I think anyone could ever hope to have. It’s a damn miracle that any of these photos are in focus because I was crying the entire time.
Once she said yes, we popped Champagne, took some more photos, told Fitzgerald what a good helper he was, and headed back down the hill.
She was beyond surprised, and Ryan successfully pulled off what must have been the most thought-out proposal in modern history. There was A LOT of moving parts, but if you want to pull off a major surprise like this, it’s totally possible! You just need to get creative.
Okay, friend, this is the hard part. If you and your partner have been together a while, you’ve probably discussed the future, and that future probably includes marriage. Most surprise proposals aren’t surprising because the question is a shock. They’re surprised because the time/ location/ means of asking is a shock. Your partner probably knows you’re going to ask, but planning an epic surprise can make your proposal can make the actual question feel like a complete shock.
If your partner is anything like my sister and you’ve been together for a long time, she is expecting a proposal around every corner. Every trip you go on, every date night you have, and every holiday piques their suspicion and a BIG surprise will be hard to pull off.
If you want a surprise that will knock them off their feet, you need a good cover-story and some good accomplices.
The more outlandish and out-of-the-ordinary the story is, the more your partner will get suspicious. Think about if you have any friends/ family members who could get them to your desired location without them getting suspicious. You also want to plan for the holes in your story and how to cover those holes if your partner notices. For example, I knew I had to make sure she saw me take my cameras OUT of the car. If I had a camera on hand, she would absolutely have been suspicious.
You know your person! Create a good story, and make sure whoever else is involved knows it too. It also helps if you can tell your story convincingly, so put on your best acting hat, and learn your lines 😉
Figuring out how to plan an epic surprise proposal takes some logistical work. If you’ll be out of town for this event, you need to be able to get where you’re going and have somewhere to stay when you get there! Here are the things you’ll need to take care of to make sure you have somewhere comfy to stay after your partner says “yes!” Even if you’re staying local for the big question, make sure your ducks are in a row!
Bed & breakfasts, lodges, and even some campgrounds will require a reservation, so hop on that as soon as you have your date confirmed. Flexible check-in times are a bonus, since celebrating can run long.
If you need to book travel for yourself without your partner knowing, see if you can get a friend to book your travel for you. If you share a bank account or have email notifications that pop up on your phone, you could blow your cover.
If you have extra people involved on the day of the proposal, it’s super important that you have an agreed upon timeline. You don’t want to get caught up in confusion, so know where you’re going and when! I have the one we created for you as an example below.
Listen, I know this is A LOT. Ryan did the most, but that’s totally their love language with each other. They are big surprise people, but you don’t have to be anywhere near this elaborate. If you’re still sitting there wondering how to plan an epic surprise proposal, know this– your partner wants to marry you.
As our lord and savior Taylor Swift once said, “I like shiny things, but I’d marry you with paper rings.” I promise your partner will be head over heels no matter how you ask. You could even spring the surprise on them one cozy morning after coffee. No matter how you ask, you get to come out of it knowing you still have a lifetime of love and surprises to have together.
Jeep Rental- Barlow Jeep Rental
Devyn’s Outfit- Madewell
Ryan’s Outfit- Untuckit
The Ring- Robbins Brothers