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Tips for Planning a Surprise Marriage Proposal in Hawaii: Part I

Tips for Planning a Surprise Marriage Proposal in Hawaii: Part I Jolene Kaneshige Photography
If you are planning on proposing while you and your special someone are on vacation it can be stressful, but I’m here to help! Below are some important questions and tips to consider for making your proposal go off without a hitch!

Prepare and Practice for the moment

Before you get to asking the secret 4 words “Will you Marry me?” make sure you have the ring ahead of time. Less time stressing about the ring means more brain power can be spent on being creative and thinking how to make the moment fun, magical, meaningful. Also, this means more time spent practicing that magical phrase. It will be a nerve wracking experience, practice saying it in front of a mirror a few times and drop to a knee. It might seem cliche, but trust me…its charming and romantic (also amazing for photos).

Here are a few ideas to get the creative process started: Does she like music, photos, notes, flowers, cake, or wine? Is she romantic, sentimental, or practical? Write meaningful notes in an envelope, print a photo book, play your favorite songs, write about the happiest moments spent together.

 Envision your ideal proposal

Think about these series of questions:

  • How much of a secret do you want to keep? Does she like surprises?
  • What type of surprise will it be? Will it be the surprise of all surprises?
  • Where and when will you propose? Do you want it to be a romantic picnic on the beach? A walk near sunset? At a fancy restaurant?
  • Who will be there? Will it be just the two of you, with friends and family, or a big gathering?
  • Will props be involved? Balloons? Flowers? A picnic basket? etc…


  • Keep it partially a secret by saying you want to take her to watch the sunset and a nice dinner after. — She will look amazing, ready for photos, and super surprised!
  • If you tell her you have a photoshoot planned, she will be ready for photos and getting to the venue would be easier.

My client Brian, told his fiancee-to-be, that he planned a photoshoot to commemorate their vacation in Hawaii! We met up at nearby location and he proposed to her half way through the photoshoot.  She was totally surprised! The best part is she said she felt confident and photo ready! (The biggest gripe I hear from brides-to-be is that they didn’t feel prepared for photos.) The logistics were also very important to him. He wanted to be sure they were here on time and also made dinner reservations.  It was also easier for me to get “the shot.”  I was able to calibrate the flash on my camera and put them in the right spot for perfect sunset photos rather than hide in the bushes or behind a tree and hope to be unseen until the last second.

to be continued in the next post…

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