“I Am So Happy That My Path Brought Me To Him”: Kaylyn & Matthew’s Proposal Story

by Taylor Team

The Relationship

Matthew and I met at work. On my first day working at a local start-up, I accidentally sat in his “spot” at the table we were all meeting at. It wasn’t the best first impression! We were best friends for a while before we started dating. Now, after a stunning proposal, we’re engaged!

Before we even got together, we were inseparable. Matthew was the person I wanted to tell everything to before anyone else and the person I wanted to hang out with all day every day. That’s what made me know that I wanted to spend the rest of my life with him; I couldn’t imagine my life without him.

I was definitely taken by surprise the day the proposal happened! We had looked at rings once, but I never knew if or when it was coming. I even got a huge splinter in my foot as we were walking to the proposal spot, so I wasn’t in the best mood at that moment!

The Proposal

Matthew managed to gather all of my family and family friends, as well as fly-in his mum, to my favourite place ever – Maui, Hawaii. They were all there for the proposal! We had gone there a year before for our first major trip together and witnessed my parents renewing their marriage vows, so the place was super special to us.

Matthew had told me that we were taking family photos at a restaurant lookout, so we all got ready for that. Unfortunately, the restaurant was closed, as the Coronavirus outbreak was just starting to impact Hawaii. We still wanted to take our annual Christmas card photos there, though, so decided to go to the lookout anyway!

As we were driving there, it was lightly raining, but thankfully it had stopped by the time we got there. Matthew said that he wanted to take a photo together on the rocks in the ocean, so we walked all the way out there. That’s when he popped the question! All of our family and friends were watching from the restaurant lookout. He even hired someone to take a drone video for us! It was more beautiful than I could ever have imagined.

It made me so happy that all of our family and friends were there to celebrate with us in my favourite place ever. Even though the Coronavirus outbreak threw Matthew’s original plans for a loop, everything turned out perfectly. The rocks in the ocean are usually packed with people. We were the only ones there then, which made it really special.

I wouldn’t change a single thing about our engagement story. I think that everything happens for a reason and I am so happy that my path brought me to him. I’m so lucky!

Where We Are Now

Matthew and I have been enjoying our engagement – I still can’t believe it’s real! We finally got to celebrate with some close family and friends and it has been so much fun! We even picked a date for the wedding, which has kept us busy with all of the planning. It will be so amazing seeing everything come together. We’re excited for our special day and can’t wait to be married!


Check out Kaylyn on Instagram here!
To read more stories in our proposal series, check out our Matters of the Heart section here!

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