My Journey
I proposed to my now-wife on Valentine's Day 2023 in Kauai, Hawaii. It was a special moment that took at least half a year of planning.
I went through so much struggle and figured many things out. If you are thinking about the same thing, here are some shortcuts and tips you may find helpful.
Know What She Wants
The most important thing is to know what she wants through communication. This includes whether she wants a big proposal, a small proposal, a surprise proposal, or one with the family.
For my wife, she wanted a private proposal with just the two of us, but plenty of good photos. Without understanding what she wanted, it would have been hard to plan her dream proposal and leave no regrets.
If you don't want to ask her directly, you can ask her friends for hints! Do it early though—you want to reach a point where she almost forgets about this conversation.
The Ring
To get her the dream ring, I reached out to our mutual friend, who is a jeweler.
She offered to do a fake user survey on what young people want in a ring. Our friend claimed to have a mass survey, but it was designed just for her.
With that, I knew exactly what she wanted and made the ring with our jeweler friend.
Hiding the Ring
After you get the ring, the awkward thing about living together is how to hide the ring box, especially when you're packing for a trip together.
The ring box is big, bright in color, and almost impossible to hide.
To conquer this, I got a configurable camera bag like this. The black velvet interior does not reflect much light, so it doesn't show depth.
I used a removable insert to make an L-shaped corner and put the ring box in the corner. Looking down, the ring box was almost invisible.
I then used the bag as my daily carry for a few months to desensitize her to the presence of the bag. I carried it whenever we were going somewhere together.
When the time came, she had no idea that the ring box had been in the bag for months.
Finding & Working with Your Photographer
For us, having a good photographer was crucial. We wanted to capture the moment and have good photos to remember it.
The hardest part about finding a good photographer is that they have to work with you to plan the proposal. What I did was go on Yelp and Google to check their portfolio and see if I liked them. If so, I usually reached out for a price with a short intro.
The combination of art style and price narrowed down the list, and I scheduled a call with 4-5 photographers.
I asked them mostly about local knowledge—their favorite locations, how they plan surprises, and what the best way to do it would be based on my schedule.
Out of all the photographers, Element Snapshots stood out. They are a husband-and-wife team, and they had a few good ideas on how to make it a surprise.
In our case, the final story we planned was this: they would bring their kid to the location and ask us to take some photos of them. After a few photos, they would offer to take some photos of us (since we were dressed up).
They would then ask for a solo shot of my wife, and I would get down on one knee and propose. A perfect plan.
Get Her to Dress Up
I understand that for many soon-to-be-proposed-to, they want to look nice, get their hair and nails done, and have the perfect makeup in the perfect dress. But chances are if they are able to do that, it's not a surprise anymore.
For my proposal, I picked Valentine's Day and reserved a nice restaurant so we would have a reason to dress up.
However, she didn't bring a dress, and I had to convince her to buy a matching, palm-print dress from H&M that morning, claiming that I spent a lot of money on the dinner and we should dress up. She reluctantly agreed.
She had no makeup, zero hair or nails done, but was still happy about the proposal. So the moral of the story is—you can't plan everything, just do whatever you can.
Knee & Propose
If you've made it this far with this much consideration—congratulations, you must be stressed out.
But trust me, the results will be amazing. When you look back, it will all be worth it.