Tayler and Josh

How We Met

Josh and I met on Oahu, he is a submarine officer in the Navy and I am getting my PhD in Marine Biology. When he picked me up for our first date I knew there was going to be something special between us. Our first date was magical, the connection I felt with Josh in a short hour and a half date was unlike anything I had ever experienced before. I already knew I liked him A LOT by the time we finished dinner and got back in the car, but when we discussed what types of music we liked on the way home and he professed his love for Taylor Swift I was completely hooked! When I got home I walked in the door and beamed about my date, telling my roommate just how much I liked this guy and how it was so different than any other date I had been on. I went to my room and secretly thought to myself, ‘I think I just went on my last first date’.

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He asked to see me again and we made plans for that weekend and pretty much have been inseparable ever since! Our first date was on veterans day, November 11, 2015 and when I went home for Christmas break just a few short weeks later I had lunch with my mom and told her I thought I might marry Josh. During this trip I told my high school friends that I was falling in love with him and we had only been dating for about a month. I had coffee with my aunt and before I could even tell her that I thought he was the one she said, “Tayler, I can just tell by the way you talk about Josh that he might be the one for you”.

Tayler and Josh's Engagement in Makena, Maui

From the beginning we just fit. We Skyped every night of the three weeks that I was gone, staying up late, being exhausted the next day and then repeating the cycle the next night. When I got back from my trip Josh told me he had to work that night and that I wouldn’t be able to see him till the next day. He had coordinated with my roommate to pretend like she was picking me up from the airport and when I got to baggage claim after a long day of travel he was waiting there in my favorite button down shirt with my favorite Thai take-out in the car and there were flowers on my desk when I arrived home.

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He is the sweetest most caring person and I feel so incredibly lucky to call him mine! We fell in love adventuring together and through our several trips to other islands we have gotten to experience some of the most amazing and beautiful things together. He is my first and only boyfriend, my best friend, the only person I’ve ever said ‘I love you’ to, he makes me laugh every day, and I’m over the moon excited to call him mine forever!!!

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How He Asked

Josh and I had talked about marriage from a very early point in our relationship. By the time 2017 rolled around we had been dating for a little over a year and I knew that Josh was interested in proposing at some point this year because we had discussed rings. However, we had talked very little about the proposal because I wanted it to be a surprise and as an avid follower of HowHeAsked stories Josh knew that I knew all the tricks. We had been talking about heading to Maui for a weekend trip during the winter in order to do some whale watching. About a week out Josh realized he would probably be able to get off work to head to Maui for the weekend and we started making plans. Little did I know that the whole week leading up to the proposal he had been running around trying to get all of the details sorted out for our proposal. I had had some suspicions leading up to the trip based off little things Josh would say or do, but tried to put it out of my head and just enjoy the weekend. The two things I told him I wanted for the proposal were pictures and to be dressed up nice.

We flew to Maui Friday night and once we got through security at the airport we decided to grab a drink before our flight. We were staying in an Airbnb the first night to be closer to where we would need to check in for whale watching on Saturday, and then we were staying at the Four Seasons in Wailea the second night as a splurge for a last island hop trip before Josh had to leave the island for his next station with the Navy. We usually like to get dressed up fancy and go out for a nice dinner on our trips and we hadn’t decided on where we were eating Saturday night yet. At the airport while we were grabbing a drink I asked him if we had decided to just eat at the restaurant at the Four Seasons because it would be the most convenient. (I am a vegetarian so choosing fancy restaurants usually requires menu searching and careful choosing.) He told me he had actually booked us a private picnic on the beach through the Four Seasons and it was at a beach nearby the resort.

He also told me that it was kind of early (5 pm) and so we would have to plan our day accordingly to be ready for the early dinner. I was immediately suspicious as I had already noticed a few weird things the week before. I asked him if it was expensive and why he did it since we were already splurging for a room at the Four Seasons. I also asked if he had requested vegetarian food for me and what I would be eating. He said of course he had requested vegetarian, but couldn’t tell me what my meal would be because he forgot. I let it go but definitely felt like there was something that didn’t quite add up. Saturday morning curiosity got the best of me and while Josh was getting ready I looked up private dining options for the Four Seasons online and noticed that it was indeed very expensive and was not a picnic as Josh had said.

I pretty much knew at this point that the proposal was happening that night, but I still could imagine how exactly he’d do it. I put it out of my mind and we went out for whale watching. Whale watching was incredible and all thoughts of a proposal left my head as I watched baby whales breach and play near our boat. As a marine biologist this was a major check on my bucket list and I would have been quite happy to just end the day right then and there, little did I know everything that was waiting for me that night. After whale watching we drove about an hour to Wailea to check into the hotel room and just hang out and get ready for our early fancy “picnic” dinner. Having high suspicions of a proposal, I made sure I did my hair and makeup just right that night just in case I was going to be photographed ;). Josh also ironed his clothes which he never does, so that was another red flag. Also he had been checking the weather constantly throughout the day worrying that it would rain, which I thought was weird since we usually made the most of our vacations, rain or shine!

So we left for dinner and drove to a nearby beach. At this point I was on high alert and very suspicious and no longer tried to hide my curiosity. He caught me not-so-casually looking for a ring box in his pocket as we drove to the beach, but didn’t say anything until afterwards. We laugh about that now. After parking in a random area and walking out onto a beach with people sunbathing, Josh said he thought we needed to go to the left even though it led to lava rock and the end of the beach. I was very confused but played along wondering where the picnic was. After we climbed over the lava rocks there was a private beach but no picnic, so at this point I was very confused. As we walked a little farther I see a bottle stuck in the sand and immediately knew this was it, and started tearing up. Josh told me it was for me, grabbed my shoes and jacket and placed them off to the side.

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We opened up the bottle together and I read the message on the scroll. I was crying at this point and after I finished reading the message I dropped it in the sand next to me and Josh got down on his knee. He said some really sweet things to me that I wish I could remember and asked me to marry him!

I was pretty much bawling at this point and blacked out after reading the message until after I said ‘Yes, of course’! I don’t remember this, but Josh said I hugged him and kissed him for a while before we realized I didn’t have the ring on.

I have read countless HowHeAsked stories where people talk about blacking out during the proposal and I thought that I was prepared and it wouldn’t happen to me. Well, let me tell you, although I saw it coming, the incredible emotions that run through you when your favorite person and best friend ask you to spend the rest of your life with them are overwhelming and it happened to me.

After I regained awareness and had stopped actually bawling and had the ring on I saw that there was a photographer who had popped up out of the bushes who was taking pictures of us. Because I love proposals and weddings I had already found the company Engaged on Maui on Instagram and been following them for awhile. Even though it wasn’t my first thought when I saw the bottle, after I had a second to calm down I remembered that the message in the bottle proposals I had seen on Instagram and as our photographer Amber walked up to us I asked, “Are you from Engaged on Maui?” Given that I don’t remember parts of the proposal I am SO glad that Josh booked Engaged on Maui to capture our special moment and that we have these lovely photos to look back on!

Once I had collected myself a bit more we ended up having a sunset engagement shoot and I really enjoyed having the emotion from the day wrapped up in our photos. After the photo-shoot we went back to the hotel and had dinner at the restaurant I originally thought we were going to eat at and when we got back to the room from dinner there were rose petals on the floor and bed. We spent the rest of the night enjoying being engaged and savoring the moment together before spending the next day enjoying the hotel and calling family and friends to tell them the exciting news. Josh and I are so excited for this next step in our relationship and in our lives and wedding planning is already in full swing for fall of 2018!!

Special Thanks

Engaged on Maui - Amber
Photographer