Katie and Brian

How We Met

We actually met online a few months after I moved back to the Bay Area. I had been living in Tulsa, Oklahoma for two years with Teach For America. I would have stayed in Oklahoma but my family was all out in California and I really wanted to be able to settle down near them. Once I moved home I realized I didn’t have the same social network back home like I used to and I was really ready to start the next chapter of my life.

Brian messaged me on Match.com during the week of Thanksgiving in 2013. We messaged back and forth for a week and then exchanged phone numbers and set up our first date for December 4th. To be honest, as cheesy as it sounds, the rest was history.

I can say that I fell for him first. I think it took him a little longer to admit how serious his feelings were for me. Whereas I just knew there was something special about him from the moment I met him. Everyone who met him could tell something was different about me when I was around him and to honest it was as if they liked him more than me! I always joke with him that my friends and family always side with him rather than me–it’s as if he was just that missing piece to my life and now it all fits together.

how they asked

Taking time off of work as a teacher always seems like more work than teaching itself but when Brian mentioned a possible trip to Hawaii, using credit card reward points, it was hard to say no to a free trip! As soon as it became official that we were going to Maui the speculation among our family and friends started on whether or not he would pop the question on the trip. I shared in this speculation but I didn’t want to ruin my entire vacation by “waiting” for some proposal so I went into the trip thinking it would not happen.

After spending the first two days in Maui running errands and exploring the island (basically through our stomachs) we decided to spend Sunday morning watching football and staying in bed. Or at least that’s what I was led to believe. Brian woke me up around 6:00am and told me that I needed to get dressed because we were leaving in 45 minutes. This was not what we agreed upon so I knew he had some sort of surprise planned. He wouldn’t tell me where we were going but he did tell me to wear dark clothing, like my leggings and a dark t-shirt. As I started to get ready my mind raced through all the possibilities of what we could be doing:

  • watch the sunrise–no, it was too late for that
  • go on a hike–no, he knew I wasn’t a fan of hiking

But then I became hung up on why he told me to wear dark clothing. I noticed he was wearing a black t-shirt, jeans, and tennis shoes. I immediately became self conscious in leggings–was I going to be dressed too casual?! He told me I should change into jeans (he told me later he wanted to make sure I would be happy with whatever I was wearing because there would be pictures).

When we got into the car he typed in the address to my phone for directions but then put it away so I wouldn’t know where we were going. I noticed we were driving in the direction of the airport so after a few jokes about our trip ending early and that the surprise was flying home early I figured out we were going on a helicopter ride. I started to get a nervous but I also knew it would be so cool and that I needed to just fight my fears and do it!

When we got inside the thought of him proposing crossed my mind but I quickly noticed how calm he was so I dismissed the idea. If he was going to ask me he would have been nervous, pacing back and forth, but he seemed so laid back.

The helicopter ride itself was insanely beautiful–literally out of a movie (because we all know so many movies and TV shows that have been filmed in Hawaii). Halfway through the ride there was a scheduled landing spot up in the hills of Maui. The pilot told us (there was one other couple in the helicopter) that we were all going to be able to enjoy some pineapple champagne and take as many pictures as we wanted.

It was the perfect place to land. Beautiful tall green grass and due to our location in the hills there was no humidity. We all started taking pictures, I of course wanted to share this experience so I was sending Snapchats and TapTalks to my family and friends not knowing what they all already knew was about to happen. So I can only imagine their excitement as they received my messages.

Brian came up behind me and asked if we should take a picture, nothing seemed out of the ordinary here because I told him how I wanted to take a lot of pictures on this trip. He wrapped his arms around me and said “I’m so happy we are in Maui together.” I was just like “yeah, me too…” But then he kept talking, “And I’m so happy that you are in my life…”

“OH $@%*!” I thought “THIS IS HAPPENING!!!!”

The pilot walked over and said he was ready to take our picture and in my head I kept repeating “Calm down, Katie. Calm down. This is about to happen. Just soak it all in.”

We walked down the hill a few feet for our picture as Brian turned me towards him. I can’t remember the exact words but what I do remember is that it was very short and sweet. Something to the effect of “I love you very much and we have talked about spending the rest of our lives together so I have something to ask you…will you marry me?” As he got down on one knee I did what anyone would expect me to do in that moment because I was nervous–I burst out laughing! The laughing quickly turned into crying as I saw Brian holding my great-grandmother’s wedding ring in his hand! It took me a few seconds to be able to actually say “yes”–which of course must have felt like years to Brian!

The Proposal

The pilot and other couple were all cheering and laughing with us and the husband even yelled out, “Hey! You haven’t put the ring on her yet!” Our pilot said he had been a part of so many proposals but he was so surprised because he didn’t know this one was going to happen–which apparently was a surprise to Brian since he told the company when he made the reservation! But he caught on quickly and took some great pictures of the whole proposal as it happened.

As we took the new few minutes to just enjoy the moment together, I asked Brian who knew this was going to happen and responded with, “Pretty much everyone but you!”

We spent the rest of the day making the phone calls to all of our expectant families and we were then able to enjoy the rest of our vacation in Maui as a newly engaged couple!

Helicopter Ride Proposal


Special Thanks