How He Proposed

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After about a year and a half of dating, Haley and I began chatting more seriously about our future together and what that meant for us.  We were talking about our career goals, how many kids we wanted, and marriage.

The closer and closer our two-year anniversary came, Haley kept dropping stronger and stronger “hints” at wanting to get engaged.

These weren’t really hints — they were really more of her showing me what kinds of rings she likes. She’s not the most subtle person ever, and I find that adorable – especially when she gets excited over something.

I told her that I want to get married, but not yet. I told her I wanted more time.

Of course, this sort of reply dropped her excitement – but to be honest, that’s exactly what I wanted.  I wanted me proposing to her to be more of a surprise. More of a shock.

For our two-year anniversary, I booked a reservation at a high-end restaurant and told Haley that I want to go to the ring store for her to look at rings and show me what she likes.  This excited her more than anything.

We arrived at Robbins Brothers in Bellevue, Washington (after me spending the last couple months searching online daily for every kind of ring that’s basically ever been made).  I learned so much about cut, clarity, and quality. More than I ever thought possible.

I knew Haley wanted a diamond band with a halo setting. Now, it was a matter of finding the right center stone.

After really thinking about Haley’s personality, the round cut for the center stone was perfect for her.  Haley’s not very flashy in her lifestyle. She’s classic. She’s timeless.

I knew what I wanted before we even got into the store.

I told Haley to walk around and show me the different rings she loves.  Almost immediately, she picked out two. And when I saw one of them that she picked, it was a diamond band with a round cut center stone in a halo setting. The exact ring style that I knew I wanted for her.

She then showed me some rings that were $750-1,000. I told her that it’s an investment. I told her that she will be wearing our wedding ring for the rest of her life, and I wanted to get her something that we can both be proud of.

Only a few minutes later, I asked the saleswoman if we can go into the back and talk about financing. (This was my secret ploy to do something else entirely).

When in the back room with the saleswoman, I bought the ring without Haley knowing a thing. I scheduled the pickup for the following day when Haley was at work.

We walked out of the store without any ring, without her knowing I bought the ring she was dreaming of and headed home.

Now, I had to figure out when to propose & how to do it.

Coincidentally, Haley and I were leaving the following month for a week-long cruise through the Caribbean.


Choosing how & when during that trip was difficult. I thought I would do it while we were mid-air during a parasailing excursion we booked, but worried about dropping it into the water below.

I thought about proposing under water while we were snorkeling, but what if it drops out of my pocket and gets lost into the Sea?

What if I did a romantic dinner at sunset and proposed to her then with a glass of champagne?

Then, I settled on something more simple. More authentic. Less staged. More us.

After landing in Puerto Rico (where our cruise was departing from), I changed into something a bit more appropriate than my flight outfit of comfy activewear.  When I got changed, I also brought my camera bag – which is where I planned to hide the ring box.

We hopped in our shuttle bus that was taking us to Old San Juan, Puerto Rico. That bus ride was certainly the most nerve wracking transportation I’ve ever taken. Not because the bus, but because I was going to be proposing only a few short minutes later.

We got off the bus in 90 degree heat, we started walking around, and as we were walking around I started to scout locations.  The same sort of scouting as I would do on any photography project.  I was searching for colorful buildings, clean backdrops, and a peaceful environment away from all the craziness.

Street after street, alley after alley, nothing was to my liking. Nothing was perfect enough.

Quite literally one street left to go until I ran out of streets up this hill, we came across an alleyway that had colorful buildings, soft Latin music playing at a cafe nearby, and a gorgeous cobblestone street under our feet.

I told Haley that I really wanted to take a photo here (100% normal request for me whenever we travel), so she didn’t think anything of it.

I stepped in front of her, put my camera bag down, got down on one shaky knee, and instead of bringing out my camera – I brought out the ring box!

“NO NO NO NO NO!!!!”

That’s the first thing that came from Haley after I got down on one knee and showed her the ring box. Classic.

She immediately started tearing up with the biggest smile on her face I’ve ever seen.

After her exclamation, I formally proposed and asked her if she will be my wife.


We hugged, kissed, and staged a photograph of us right after our engagement in that same alleyway.
* I really wanted a photographer to capture the proposal, but every photographer that I was interested in booking from Puerto Rico was either booked or out-of-town for a wedding photo conference.  So, instead of not having any photographs, I took a photo of Haley against the wall in the alley, Haley took my photo, and I composited them together in Photoshop to make it look like it’s one single image!

An hour later, and we were on our cruise ship leaving to sail through the Caribbean for what I like to refer to as our “proposal-moon.”

St. Thomas, Barbados, St. Lucia, St. Kitts, St. Maarten, here we come!!! WE’RE ENGAGED!

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