Proposal in Paradise

April 17, 2019
Posted in Life
April 17, 2019 Ashley

On Saturday morning, April 13th, 2019, we woke up at around 7am. We were at one of our absolute favorite getaway spots on Pine Island, FL in a town called Bokeelia. Matt introduced me to this great “Old Florida” spot for the first time in July 2018, when we stayed a week for the 4th of July.

Matt and I immediately after getting back onto the boat after he proposed!

With the ocean, boating, and the outdoors being a few of our favorite things – this area of Florida immediately became one of my favorites – if not my very favorite, new spot, most importantly my favorite place to be with Matt.

Matt, my now fiance’ also grew up in Florida near the gulf coast, so this is an area he had been coming to for years and is very familiar with – on land and sea.

I originally only thought I was going on this specific trip because the condo was reserved months before for Matt and his brother to take a trip down there together. Matt’s brother ended up not being able to make it though, so Matt said ‘hey, it’s already reserved, why don’t we still go?’ That was an obvious “yes” from me considering how much I love it there.

Well, fast forward to Friday, April 12th, 2019. Matt picked me up from work in Orlando after the morning show around 11:15am so we could get a head start on the road as we had the boat on the trailer behind the truck too. It takes about 3.5 hours to get from work, down to the condo in Bokeelia, and we wanted to make it there before sunset.

The view looking out at the water from Cabbage Key

We got to Bokeelia, put the boat in the water, and unpacked at the condo. That didn’t take long since we were only staying the weekend – so we hopped on the boat for a ride up to one of my absolute favorite Florida treasures – Cabbage Key. It’s a great family-owned island that you can only get to by boat that has a bar and a restaurant with amazing views surrounding the island. We left Cabbage Key just in time for sunset which was about 7:51pm and headed back towards the condo to grab some dinner.

The sunset view from the boat near Cabbage Key

While this whole time I didn’t really suspect anything having to do with a marriage proposal, I will say I thought Matt was acting a little bit odd compared to usual that Friday night – a little quieter, and I should add the whole week before he wasn’t sleeping well – so of course I wondered….’hmm…..I wonder if this could be the weekend’ because I always hear how guys act a little weird when it’s about to happen – BUT, I honestly didn’t think it was. I never had any idea or expectations of when it might be, but I knew it was something we both wanted and that it would happen eventually.

Friday night we got back to the condo and I asked Matt a typical question on one of these trips, ‘what time do I need to be ready in the morning & do we have a plan or just gonna chill and go with the flow type of day?’ Sometimes we’ll plan to fish early in the morning, other times we’ll take the time to catch up on sleep and sleep in.

Well, to my surprise Matt said, ‘oh tomorrow morning I actually have to meet up with [Buddy – an old friend of his who lives in the area] because he wants to see how my boat runs with this motor because he’s thinking about getting the same one. This was a completely believable story – I didn’t second guess him for a second HAHA.

So Saturday morning, April 13th, 2019, off Matt went around 7:45am, and said he’d be back around 9:30am and that’s when we would head back out for the day.

Matt got back to the condo around 9:45am and I was actually out at the dock area when he got back because it was such a pretty morning. I wanted to be outside and I was done getting ready. I didn’t suspect a thing when he got back. I asked him, ‘how did Buddy like the way the motor ran?’ Matt responded so confidently I look back now and say WOW you really were good making that up on the spot haha. Matt said ‘yeah he really liked it, he know’s it’s a good motor, etc.’

A photo I took of Matt returning to the condo Saturday morning before we went back out. Little did I know he had just returned from scribing ‘Will you marry me?’ in the sand.”

So we get loaded up on the boat Saturday morning and head out to this spot Matt ended telling me ‘Buddy said there’s a spot over near Cayo Costa where the porpoise feed on the baitfish and there’s a ton of them that we should check out.’ Growing up in Florida, it never gets old [at least to me personally] when seeing dolphins in the wild. I love it. So Matt knew that was something he could say because he knew I’d be into it.

As we were on our way out there, the wind was pretty strong, which made the water a bit choppy – making it a somewhat rough ride out to Cayo Costa – another island you can only get to by boat. I even said to Matt at one point, ‘babe it’s ok we don’t need to come all the way out here with the wind being like it is.” But he insisted it was ok. HA – well, little did I know it’s because he had something WAY bigger planned.

We pulled up to Cayo Costa, Matt threw the anchor in, and we were close enough to jump in and walk up to shore. Matt carried me on his back just in the water until we got on the sand. We started walking and I’m still thinking we’re going to look at these dolphins chasing baitfish LOL.

We walk a few hundred feet, and I start to see some letters written in the sand. I see my name….’A-S-H-L-E-Y…..’ and I look at Matt because I can tell he’s watching me to see my reaction as I’m approaching this message in the sand…..I then look again and see ‘W-I-L-L Y-O-U M-A-R-R-Y M-E?’ spelled out.

A drone shot of Matt Saturday morning scribing “Ashley, will you marry me?” in the sand before he came back to pick me up.

I think I was in shock. It was completely surreal and I then looked to him again almost for assurance that it was for me HAHA. I think I said something like, “are you serious?!” And he was like “of course I’m serious!!!”

He then told me everything he loved about me and some other sweet words I will keep between us, but then proceeded to get down on one knee and grabbed my right hand (which we laughed that he had grabbed the wrong hand) and asked if I would marry him. Now, the CRAZY part is WHERE Matt had the ring – it was looped on the bungee cord inside his board shorts – the cord that comes in board shorts normally where surfers can keep their surf wax, etc. and then the pocket velcro’d shut.

This is how Matt secured the ring in his board shorts pocket.

It was absolutely perfect. Beyond anything I could’ve ever imagined. Unexpected and the most thoughtful and romantic gesture I have ever experienced, and better yet, it happened at our favorite place to be.

Just hours after the proposal, after enjoying a “Cabbage Creeper” cocktail at Cabbage Key – one of my favorite places only accessible by boat.

At one point I asked, “who helped write this in the sand!?” And Matt said “I did it!” That was where he went that morning….he didn’t actually ‘go meet up with an old friend to test out a motor’…..he went out to Cayo Costa that morning and scribed the words in the sand, he hired someone to run a drone above, and his best friend from high school was a few hundred yards away hiding on a jet ski with a bottle of champagne all for the proposal.

Matt’s high school best friend surprised us with this bottle of champagne and glasses immediately after the proposal when he pulled up on his jet ski.

It was really amazing and I am still on cloud 9. Thank you so much for all of the love and support. We are both so appreciative and thankful to have so many people in our lives, our friends and families included, who love us and support us and have been following our journey thus far.

THE RING of all rings.

When it comes to the ring, I was never one that wanted to go look at rings and try them on before I was ever engaged. I knew deep down whoever I was going to marry would know me well enough to pick something they wanted me to have, and I love knowing that Matt picked it out by himself. He didn’t even ask any of my friends. He asked for referrals on where to shop around, but he ended up picking the diamond first, and then the setting. I am unbelievably blown away and truly feel like the luckiest girl in the world. Regardless of the ring – Matt put so much thought, effort and care into the proposal from the beginning in asking both my mom AND dad for their approval. If I can give anyone out there any advice that might still be looking for their person, soulmate, partner of a lifetime – hold out for it – because when you find it, it will absolutely turn your world upside down, in the most loving, positive and fulfilling way possible!

There’s so many tropical plants and flowers on Pine Island that I couldn’t resist taking photos.

We can’t wait to spend the rest of our lives together and are currently soaking in all of the excitement before jumping into any serious wedding planning quite yet!

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