We love a great staycation proposal story, don’t you? When we read this story, we knew that we wanted to feature Mollye & Tyler’s staycation marriage proposal story.
Share with us when and how you met each other.
We met on Tinder! After a few weeks of texting, our first date was on April 20th, 2018. He planned our first date on Disney property because he knew from our conversations that I love Disney. He even planned Dole Whip into the night!
What are your favorite things to do together as a couple?
We enjoy spending the day at the beach, visiting wineries and/or distilleries, going to theme parks and water parks, attending weddings, taking walks outside, spending time with family, playing games, cooking, traveling, dancing, exploring a NEW place, or activity and watching reality TV together.
How long were you together before getting engaged?
2 years and 8 months.
Did anyone help with the staycation marriage proposal?
Tyler had a vision and a plan for the proposal in which he recruited his mom, dad, sister, and 2 cousins to help!
Share your marriage proposal story…
Let me start by saying that I’ve NEVER been more surprised in my LIFE. I was absolutely clueless until about 20 seconds before he got down on one knee. Nothing could’ve prepared me or caught me more off guard than the story I’m about to tell.
To preface the story, Tyler asked me a few months beforehand what my “dream proposal” was. He wanted to know if there was anything I had been hoping for or envisioning since I was a little girl. I said “I don’t really have a dream proposal. I’d probably love lights of some kind. Like lantern lights, or bulb lights….something romantic. Probably not a big public ordeal, more private. It would be cool to have my family join afterward. Not during the actual proposal, but afterward would be ideal”…….
Tyler and I love to take weekend staycations in Orlando. Since we are Central Florida locals, it’s something we’ve done consistently throughout our relationship. We just stay 2 nights in a hotel in the area, go to the theme parks, go out to eat, and hang out by the pool to relax. Valentine’s Day 2021 rolls around and Tyler suggests that we do our usual staycation. But he suggests that we do it the weekend AFTER Valentine’s Day because hotel rates were “cheaper”. Little did I know, he just didn’t want to be “basic” and propose on Valentine’s Day! Leading up to the weekend, he had EXTRA enthusiasm for our plans and I thought it was so sweet but also random how excited he seemed for something we do pretty frequently.
Tyler picked me up at my house and we rode together to the hotel. We pulled into the Hyatt Regency Grand Cypress which is a bit more expensive than most places we stay on these types of staycations. He said “don’t worry, I found a really good deal online since we are staying here the weekend after Valentine’s Day!” (fully selling me on his story). We checked into our room and I was giddy like a child, just excited to be there. We unloaded our things then I went with him to park the car.
I suggested we take a little walking tour around the property. On our walk around, we came upon this brick pathway called the Oak Terrace and I said to him “What’s back here? This looks pretty!” It was a big romantic oak tree with lanterns hanging down from its branches in this little intimate space. My first thought was “wow this would be a beautiful spot for a small wedding” and I proceeded to take photos of this little area on my phone. Of course, I had no idea that about 2 hours later, he would be down on one knee asking me to marry him in that exact spot.
We went up to the hotel room and talked for a little bit before noticing it was starting to pour rain outside. The sky was full of dark clouds. Tyler said, “I’m just going to close these blinds”. I found out later it was because he was having too much anxiety looking at the weather possibly spoiling his plans. He was getting weather update texts from his mom who was outside our hotel starting to prepare everything for the big moment!
We normally get each other small presents. I noticed his gift bag in the room so I picked it up and said “wow this is wrapped super cute! And it’s so LIGHT! I wonder what’s in here….should we do presents now or later?” He said, “Oh let’s just wait to open presents until dinner like usual.” I agreed and didn’t think twice about it.
We started to get ready for dinner. He told me we had reservations at 7 pm somewhere on Disney property but wouldn’t tell me where. He just said I needed to be ready by 6:30. I had just bought a new dress the week before. I couldn’t try it on in the store because of COVID but I bought it anyway which is very unlike me. I’m so glad I did though because it was perfect for the occasion (getting engaged)! Tyler had a new outfit for the night too, to which he said “since you got a new outfit, I figured I would too. Why not?!” He truly wanted me to have no hints or possible suspicions.
While I got ready, Tyler played all sorts of country love songs and I remember thinking how sweet he was. I suggested that we take a few selfies together before we left for dinner. I found out later that he was trying to make sure I didn’t see that his hand was shaking from nervousness while he took those selfies.
We left our hotel room and started walking through the hotel out to the parking lot. Tyler suggested we go the long way around because “he wanted to see what the pool lights looked like at night”…..I was honestly annoyed because it was cold, raining and I was in heels. I didn’t understand why we couldn’t just go the short route to the car. But he leads me straight to the Oak Terrace where all the beautiful lantern lights were turned on hanging in the tree. I no longer cared about the weather or my feet.
I saw rose petals on the ground, I saw candles, photos of us, champagne with glasses and then I saw his mom, dad, and 2 cousins who were taking photos and videos. I knew immediately what was happening. Tyler held my hands and said something along the lines of “Mollye, I love you and I want to spend the rest of my life with you”. I don’t remember exactly what he said because it was all a blur at that point, but I know it was short and sweet! He reached into the gift bag which I had been toying with earlier in the night to get the ring box out. We both had tears in our eyes and then he got down on one knee and asked “Will you marry me?”. He special ordered a ring box that lit up so when he opened it, the ring was absolutely SHINING. It was hard to see through my watery eyes, but I soon realized that he bought me the EXACT ring that I designed and asked for. I was shocked and overwhelmed! I said “OF COURSE I WILL!” while trying not to cry in response to his marriage proposal.
We popped champagne immediately after I was done gawking at my new jewelry. His family was documenting the entire thing, we took a few more photos while I started asking a million questions “Who knows about this?! How long have you been planning this?! Who should I call first?! How did you pull this off?!” His family left to go to dinner (we were leaving soon after to meet them). But before we left, we stood for about 2 minutes alone together, in the rain, looking at this magically lit tree with rose petals on the ground reveling in the moment of what just happened. We were engaged.
On the way to dinner, Tyler was doing everything he could to DISTRACT me from calling people to tell them the news. I did Facetime with 3 or 4 of my friends right away, but no family members. I ended up putting my phone down and enjoying the car ride with my fiance. When we arrived at dinner (a restaurant I love, of course) I start walking towards our table and I notice my good friend Amanda and her husband Chris at the table, they live about 2.5 hours away. I was shocked to see them until I noticed MY PARENTS all the way from Michigan at the table as well. Finally, I look to my right, and sitting there is my SISTER who flew all the way across the country from Washington State to Florida.
My family members knew for over a month that all of this was happening. Tyler contacted these people knowing I wanted them there (because I told him 2 months earlier). The table at the restaurant was decorated with cookies shaped like diamond rings, a “we’re engaged” sign with matching napkins, and all sorts of other fun things. Tyler had ANOTHER bag of presents for me which included a matching set of fiancee stemless wine glasses, rubber rings to wear at the gym instead of my diamonds, and a t-shirt that said, fiancee! I was truly dumbfounded. I felt SO incredibly loved, special and SPOILED.
The next day we spent just the two of us together in Magic Kingdom at Walt Disney World celebrating our engagement! We wore “happily ever after” buttons, got congratulated all day long, and rode all our favorite rides! It was truly the best night and weekend of my life and a perfect start to what will be our life together forever.
What was the best moment of the proposal?
The best moment of the proposal was when I realized how much TIME and EFFORT and PLANNING went into the whole thing knowing it was all for me. It was a thoughtful, detailed, and beautiful plan created by Tyler just to make sure that his future wife had the most memorable and perfect night of her life. Also being surprised by my friends and family afterward. Aaaand also seeing the ring for the first time. There were so many magical moments.
Who did you tell that you were engaged first?
I FaceTimed one of my best friends, Molly, first. She is the matron of honor!
Tell us about the ring!
The ring: whew! She is a beauty. I found 2 rings I absolutely loved and asked the jeweler/designer to mesh the 2 designs together. It’s has a fairly large band that supports around 9.5mm stone inside a cushion cut halo. It sits up high and has hidden diamonds underneath as well.
It’s sparkly, big, and just my style! The designer is Michael M and it was purchased at Casa Leon Jewelers in Lake Mary, FL. They are the absolute best and I could not recommend them more. We had the best experience working with them.
What has surprised me most about being engaged (so far) is how excited and involved Tyler is with all the planning. He’s always willing to give his opinion and he has gone out of his way to attend wedding-related events with me (bridal shows, venue tours, etc). It has been really fun and cool to see him be so engaged in the planning process. Also the amount of people that congratulate you, news travels fast!!
What I’ve enjoyed most about being engaged is using the word fiancée instead of boyfriend/girlfriend LOL! It’s finally sinking in that I get to be with this person forever! We’re still in “engagement bliss” where we just want to cherish this time in our lives. I enjoy daydreaming about the wedding day and talking about all the plans too. After attending so many weddings, it’s so exciting to finally be the bride! Also, dress shopping has been really fun!
What are you most excited about wedding planning?
I’m most excited about finding my dress, picking the song I walk down the aisle to, possibly starting to learn a choreographed dance with Tyler?! And asking our bridal party members to be at the wedding 🙂 and I suppose choosing all the decorations and flowers. So many things to look forward to!
If you’ve already decided, when are you getting married and what is your venue?
We are getting married on 3/2/22 at Paradise Cove in Lake Buena Vista, FL.
Why did you choose that venue?
I found the venue online and when we went to tour it, we just KNEW it was the one. I wanted something with water but also trees and greenery. We both love Florida, palm trees, and water! Paradise Cove feels like a tropical backyard party, but elegant enough to be romantic as well. It completely fits our laid-back beach vibe and there are tons of different photo opportunities/spots. It was the first and only venue we looked at.
We are inviting around 150 people.
Our wedding style is more of a backyard beach party–but make it classy and elegant. We want to make sure our wedding is a more formal event, but with a ton of fun vibes and a few surprises!
Have you selected any other vendors for your wedding?
Castaldo is our photographer and videographer, Cocktails Catering will be doing food, iRock Your Party will be the DJ, and Atmosphere’s Floral and Decor will be handling the flowers. Our officiant will be Tyler’s former boss and mentor 🙂
Congratulations Mollye & Tyler on your staycation marriage proposal!
Special thank you to Dylan Nelson Photography for the amazing engagement photos.
Want to feature your proposal? CLICK HERE to submit your story!