The Secret Art of the Hawaii Surprise Proposal

The one portrait request I'm the most excited to get is the surprise proposal! Plotting with the happy/nervous guy about the just the right place, the secret code word we’ll use and then getting to watch their happy moment unfold as I photograph it is just so, well...romantic!

Designing the perfect secret surprise proposal on a romantic beach in Hawaii where I can capture the action has some particular challenges, however. You want a location that has a stunning Hawaii backdrop that has the least amount of tourists/people in the background. We also want the best possible light on our couple as well, since we’ll be relying strictly on natural light, which requires specific timing for a particular location. At the same time, we want a location that offers at least a little bubble of privacy to allow an intimate and emotional moment to blossom and express naturally without being rushed or stilted.

Of course, the most important part of all, is keeping the intended victim - oops, I mean, girlfriend - completely unsuspecting until the actual moment!

While there are lots of ways to set up a secret marriage proposal on Oahu, I have found three basic approaches that work the best to set up and photograph a romantic Hawaii beach surprise proposal.

1. Propose to Her During a Photo Shoot

Super simple: arrange for a "couples photo session" just because you love her and you’re on vacation and you think it will be great to have romantic photos on the beach at sunset together. By being totally up front and planning it with her, she’ll never suspect a thing. The two of us will arrange our own secret code word that I will say at a point in the session when I've determined the light and location is ideal. I'll casually drop our code word (usually “Epic” - “Oh, these are going to be EPIC photos!”) and that will be your signal that I'm ready to go. Then it will be your moment to shine and surprise your sweetheart with your marriage proposal. The upside to doing your Oahu surprise proposal during a photography session is that your girlfriend is prepared with her hair, makeup and clothes just how she wants them.

2. The Hide In The Bushes Surprise Proposal

The second approach, which is best for overly suspicious girlfriends is that you arrange to go for a stroll with your sweetheart at a nearby park or beach. We have mapped out a specific spot ahead of time where you’ll do your surprise marriage proposal. I will either be hiding in bushes nearby or pretending to be a landscape photographer taking photos of flowers, etc (tourists with cameras are everywhere, after all!). You two will walk up to the preplanned spot near the appointed time and the moment I see you go to one knee, I simply pivot and begin photographing your surprise proposal. What I have found from experience, is that your sweetheart won't even notice me for awhile, as you’ll be her sole focus the moment you go to one knee.

3. The Fun Adventure Surprise Proposal

This is the most popular option, for myself and most of the surprise proposal clients I’ve worked with. The adventure surprise proposal is where you and your sweetheart go for a hike or go exploring at some off-the-beaten-path mountain top, waterfall, or deserted beach location. I’ll be there before you, pretending to be a landscape photographer (which is how I actually got many of these photos!) hunched over my camera and tripod, and as you arrive I’ll be watching out of the corner of my eye. The moment I see you begin to propose, I simply turn and begin taking photos of your proposal. The advantage to the Fun Adventure Proposal is that you’re both doing something you love, in a stunningly beautiful location, and your girlfriend never saw it coming. Now that’s a surprise proposal!

Many couples do this option when they choose my Hawaiian double-session package, with the adventure surprise proposal is one session, and then a follow up “engagement” session at a different location and time (usually at sunset). This gives you the maximum variety of images, and allows your sweetheart to get all dressed up for the second, more “formal” session. Think of it as your “surprise proposal photo session" and “engagement portrait session” all in one.

Check out these two examples of fun adventure surprise proposals and engagement portrait sessions here: Philip & Sam’s epic mountaintop, sunrise surprise proposal and Minto & Elda’s mountaintop surprise proposal. (These are blog posts on my other website,

She Said Yes!

Once your sweetheart has given you an enthusiastic and slobbery yes and she's floating on cloud nine, we then finish your surprise proposal photo session with as many romantic and fun “engagement” images as we can. For the rest of your life you’ll have these romantic photos of your special moment in time to remind you of your love and connection. So if you're ready to pop the question and propose to your sweetheart, click the Quick Form button below and shoot me a note. I would love to help you make your Oahu surprise marriage proposal a wonderful moment to cherish!

A short behind-the-scenes video taken during Matt & Cynthia's surprise proposal photo session at Magic Island in Waikiki, Oahu Hawaii, at sunset. While I had often incorporate the hand signing "I Said Yes" shot, I had never paired it with the guy holding up the ring box too.