We were headed to Orlando for the weekend to “celebrate his birthday” and go drinking around the world at Epcot, or at least that was his story and he was sticking to it. He booked a hotel and made the plans, which was nothing out of the ordinary, since he’s definitely the travel planner out of the two of us. He said he booked a fancy steakhouse for his birthday dinner and that his parents would be coming to celebrate too. The fact his parents were coming definitely threw me off of any potential proposal trail.

[Photo of the restaurant, Capa. Photo cred: Four Seasons]

Despite my life being shared in a very public way on the radio every morning, when it comes to intimate moments, Brian and I really like to savor them for ourselves. I knew there was no way that his parents would be sitting across from us at a table when he proposed, especially if my family wasn’t there, as well. This was the explanation ruminating all week leading up to that Friday.

In all honesty, we’d been dating for such a long time though, that if he so much as looked at me in a strange way, I thought maybe this would be the moment he was proposing. I was ready to say yes a billion years ago, even though we’d only been together for eight.

How’d He Do It?

Brian told me we were staying at the same hotel in Orlando that we usually stay at, but then a day or so before the trip, he told me that he splurged on a room at The Four Seasons for his birthday. I definitely thought, “Whoa, is something up? The Four Seasons?!” I quickly shook off the proposal thought though, because he had said a few things that week that threw me off, like telling me I didn’t need to get my nails done. We had looked at rings a few months prior and I had come up with a design for my dream ring, but I didn’t know what came of it. After eight years, you kind of just go with it and stop overthinking every single dinner.

That day started like any other Friday, I had work and school. I was exhausted and didn’t get done taking a test in class until much later than anticipated. By the time I finally got home, Brian was noticeably anxious. He was worried we’d be stuck in Orlando traffic on a Friday, of all days, and that we’d miss our dinner reservation and first day at the resort. We set out for Orlando and sure enough, we got stuck in traffic. A ton of traffic. To make matters worse, I was on one of those “drink 2 gallons of water a day” kicks, so of course I had to stop to go to the bathroom throughout the trip. At this point we were honestly both annoyed with each other. He didn’t want to keep stopping and I didn’t want to pee my pants. haha

After over an hour and a half in traffic, Brian called the restaurant to let them know we’d be late. Brian relayed the message that they may not have a table for us if we’d be any later. I was bummed, because it seemed like his plans for a fancy birthday dinner weren’t going to happen. Little did I know he had something much bigger planned.

Once we checked-in, I rushed to get ready and while doing so, his mom called him. She said they were stuck in traffic and wouldn’t be making it to dinner. I knew he wanted them there for his birthday, but I knew how bad the traffic was. I threw on a dress my sister had already pre-approved for a fancy dinner occasion. It was a dress I’d bought years ago, but had never worn. Old shoes, old purse; not expecting a proposal, but always thinking maybe, just maybe…

Outfit Details:

 

Right before leaving the hotel room to head to the roof of the hotel, where the steakhouse was located, Brian snapped a selfie of us. He said that his mom asked him to send one, since she and his dad couldn’t make it. I found out later that the selfie wasn’t really for his mom, but I’ll explain that towards the end of the story.

We got to Capa and thankfully they still had a table for us. They cleared two of the place settings, so I really did think Brian’s parents were supposed to be there. He later said that wasn’t part of the plan, but it was great because it threw me off even more.

We ordered some drinks and the waiter suggested we wait to order our entrées, since the Disney fireworks were about to start outside and we may want to watch them from out on the balcony. He was right. I’m a sucker for fireworks. Brian knew this. We had an appetizer and then made our way out to the balcony to watch the show. Once we walked onto the balcony, I knew something was up. There were no people seated outside. None of the tables were set. It was just me, Brian and a massive balcony by ourselves.

[View of the Disney fireworks from the balcony where Brian proposed. Credit: Four Seasons]

I remember asking why no one else was coming out to see the fireworks, but he said he didn’t know. I had my phone ready to record some of the fireworks, when Brian took my hand, removed my phone and turned me towards him. He started saying a really heartfelt-speech about how far we’ve come and where he sees us together in the future, all while getting down on one knee. Cue me ugly crying. I swear it all happened so fast that it felt like I blacked out for a moment. Next thing I know, Brian was still on his knee and asking, “So, is that a yes?”

It was a, “Yes!” A very excited and teary, “Yes!”

[Photos by: Victoria Angela Photography]

A few moments later, I realized a photographer had joined us on the balcony and was snapping photos. Turns out, the selfie Brian took in the room earlier was actually sent to the photographer he hired to capture the proposal. He had never met her before and she needed to know who to look for and what we were wearing. Sneaky, sneaky.

[Selfie Brian sent to the photographer, before I cried off all my makeup]

Right after I said yes, pictures kept being snapped and a waiter came and handed us champagne filled glasses. I was in complete shock. You can see in the pictures that my eyes are watery, because I couldn’t stop crying happy tears. I also couldn’t get over the fact Brian lied to me and hid this whole thing! We were never staying at a different hotel. The dinner wasn’t for his birthday. His parents didn’t get stuck in traffic. His parents were never coming. I’d later find out it was all a cover-up to throw me off.

He told me he had actually planned to propose a month earlier and booked everything then (including the photographer), but I had gotten really sick on a trip and was in the hospital, so he had to plan it all over again. I believe it all worked out exactly as it should have. We ended up getting engaged on September 28th, 2018.

When we walked back inside the restaurant everyone was clapping and saying congratulations. Apparently the entire waitstaff, as well as restaurant goers, were in on the proposal in order for everyone to avoid walking onto the balcony. It was so nice of people to not interrupt the moment. They had also just got a front row view of the engagement and my alligator tears through the massive glass windows.

Still in complete shock, we walked back to our table and a congratulatory dessert board was sitting out for us, as well as more champagne (it’s like they knew me haha).

We watched the remainder of the fireworks from our table, ate dinner and relished in the fact that Brian had pulled it off and that we were engaged. He could finally breathe and I could finally stop having to answer the question, “When is he going to pop-the-question?” haha. But really, it was so exciting to move forward with our life together. I will say, I couldn’t stop looking at the ring once it was on my finger! The ring that was once something I drew, was now tangible and sparkling on my left ring finger. AHH! I’M ENGAGED!!

The rest of the weekend was really special, thanks to the hotel. The Four Seasons was all about the details and every staff member we encountered, whether at the bar or the coffee shop said, “Congratulations!”. Everyone was so sweet and it really made all the difference.

Saturday, we made some phone calls to share the news and did a lazy pool day. The following day, we made our way to Epcot to drink around the world. First stop: France for some champagne!

While getting ready to checkout on our last day, we heard a knock on our door. Room service was there to deliver pastries and congratulatory mimosas with a personalized sendoff message. I was on cloud 9.