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Inspiration » Proposal Story » Joy Proposal Story: Kristen & David

Joy Proposal Story: Kristen & David

by Cali Pitchel

How did the two of you meet?

Despite growing up only 15 minutes away from each other, David and I didn’t actually cross paths until 2012. Although we both knew of each other, it wasn’t until October of that year when we first smiled  and said hello during a quick meeting while David was on vacation in the Magic Kingdom where I was working. I vividly remember that moment, and I remember thinking that it was funny he was so shy for someone so handsome, but he could only even make eye contact for a second or two before glancing away.

Fast forward to 2014: We started exchanging short and sweet text messages and started to discuss that David needed a life change. Obviously I suggested coming down to Florida and giving a job at Disney World a shot. After all, he could interview and see how he felt about it and he’d have some time to decide since they don’t hire on the spot… until he got hired on the spot.

Michelle Roller

Michelle Roller

 As fate would have it, I was actually needing another roommate for our next lease, so the timing couldn’t have been better. As for the next two months until the new lease started, well I made David the nicest twin blow-up mattress bed anyone has ever known. That my friends is when we started to feel a bigger connection. We’d snuggle into our (separate) beds and talk like kids at summer camp until one of us fell asleep.

We became each other’s best friends and stayed that way for months. With the new apartment we moved into separate bedrooms, but with time our chemistry started to get pretty undeniable. After all, “You can’t date your roommate,” and “You don’t date your best friend,” seemed like logical guidelines at first—until they seemed to clearly not be for us. I started dating my roommate and now I get to do that forever!

Who made the first move?

That was David who was able to push down those butterflies and go in for a kiss.

Give us the proposal details! When? Where? How?

David and I had visited Oahu in 2015 for my April 12th birthday – just the two of us – and we had such a phenomenal time, so we wanted to come back again and share it with loved ones. Everything aligned perfectly to head back a year later for another birthday trip, and this time we brought David’s two sisters and their boyfriends, along with my mom.

We arrived at Aulani earlier in the day and we all went straight down to the beach to swim and play around in the ocean together. After taking quick showers, we rushed back down to go watch the sunset from this beautiful spot David and I had watched the sun sink into the ocean from the previous year. My mom suggested that I should wear a dress since his sisters were wearing dresses and they were probably hoping I would too. In retrospect, I’m pretty thankful for that clever mom logic to get me out of the yoga pants and tank top I had tossed on.

As we waited for the elevator, David was acting so nervous and quiet that the thought crossed my mind that he might be proposing, despite telling me he’d never propose on my birthday, and throwing me off his tracks weeks earlier. For some reason my reaction was to pat down the pockets of his shorts – which really, what would I have done if I had felt that box?! Would he have had to propose there at the elevator?! Don’t worry, he had nothing in those shorts pockets (and I thought nothing of the jacket he was holding at the time cleverly concealing the ring box).

The bigger picture is that regardless of the little things that go so wrong or so right on our actual wedding day, it’s more so about solidifying this beautiful love and then continuing to find the joy together every single day going forward.

We walked along a meandering sidewalk toward the ocean and David pulled me off to the side by an unassuming palm tree. He pulled me in for a really tight hug and he took a deep breath and grabbed my hands and that was the moment I knew he was proposing. I feel horrible because I don’t even remember half of the beautiful words he said because I was just so surprised and excited and feeling a million happy feelings that my brain was just mush. He got down on his knee and I just wanted him to be standing again so I could kiss him. Really kiss him. I’m actually fairly certain I said, “yes but stand up, stand up!”

Michelle Roller

Michelle Roller

It turns out he had planned to propose at that beautiful sunset spot, not en route to it. His sisters – who knew his plan – had almost missed it too because they weren’t expecting him to change plans. It just makes me smile to think that he mentally and physically couldn’t wait another minute because he was so nervous he had to just do it right then and there, just off the sidewalk by that random palm tree.

What has been your favorite experience planning the wedding?

We both agree that taking our engagement pictures was one of the absolute best days of our life together! We took a quick overnight trip to our favorite place on earth, Yosemite National Park (which is also where we’ll be having our wedding ceremony this summer) and it was such an incredible whirlwind of two days! We honestly can’t believe all of the magical images our photographer, Michelle Roller was able to capture because the whole time we were talking and laughing and making funny faces, and most of all just having the time of our lives loving on each other in such an incredibly beautiful environment.

How do you stay sane under the pressures of wedding planning?

Whenever I start feeling overwhelmed I lean on David to help with research or ideas. After all, it’s OUR big day and he’s obviously my other half. Plus we come up with better ideas when we’re discussing and planning together! So far we’ve managed to tackle every little thing that’s come up!

Michelle Roller

Michelle Roller

How did you hear about Joy?

I stumbled upon Joy because I was bored with the run of the mill wedding website-builders & knew we could find something better. Joy has given us so much more than a beautiful website to share information with family and friends, and we can’t wait to see how our guests embrace the app!

What is your favorite part of using Joy for your wedding?

We have a bit of a unique situation as we’re having a small destination wedding, and then a larger reception with all of our family and friends once we return back home. Since most of our loved ones aren’t  able to attend the ceremony, we love that through the Joy app, they’ll be able to see pictures of the wedding ceremony that same day, and enjoy it with us from miles away. Then when the reception rolls around, we love the way that the album will grow and develop into this beautiful reminder of our wedding and celebration.


What piece of advice would you give couples to ensure that they use Joy to its fullest potential?

Don’t try to tackle building your whole website in one day. There are so many great features you can add on to your own site and by stepping back and coming back to it, we were able to really craft a wedding website we’re proud to share without ever feeling overwhelmed!

At Joy we believe that even though a wedding lasts a day, joy lasts forever. What does that mean to you?

It’s funny how much time we put into planning just one day of our lives – well for us, two days! The bigger picture is that regardless of the little things that go so wrong or so right on our actual wedding day, it’s more so about solidifying this beautiful love and then continuing to find the joy together every single day going forward.

Michelle Roller
Michelle Roller

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