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April 26, 2023

She’s My Everything – Trent & Kaylee’s Oahu Proposal Portrait


Last Updated on April 30, 2024 by Karma Hill

We were delighted to coordinate a surprise Oahu portrait proposal for Trent, who couldn’t contain his excitement about popping the question to his girlfriend, Kaylee! Our photographers are skilled not only in capturing beautiful life moments but ninja-style operations like a proposal! Trent was adamant this had to be very discreet, and we knew exactly what to do. So how the big moment happened was our photographer pretended to be a beachgoer, minding their own business, yet waiting for the right moment when Trent got down on one knee……

oahu proposal portrait

Proposal Or Punked?

But not all went to plan – he totally forgot what to say, and he opened the ring box upside down! Oops! Kaylee even thought he was kidding for a second cause she didn’t see a ring – just the empty side of the box! Oh my! Thankfully Kaylee was a good sport about it, and they both were beside themselves laughing… and she said yes, of course! (At least he didn’t forget the ring!)

Our New Adventure

After the joyful and silly moment, out we popped from our hiding place to capture their happiness and big news! Trent, who was born in Oahu, was so excited to share the island and all of his spots from his childhood with Kaylee. Since Kaylee has never been to Hawaii, this was a very special vacation and also one that will forever change their lives! We couldn’t be happier for them!

The dramatic mountains and privacy of Waimanalo Beach provided a picturesque spot to match the occasion’s significance. We love this beach for inimate moments like their Oahu proposal portrait simply because of the views, and it’s off the touristy track. The natural beauty made the moment feel even more like a dream! They look so happy and in love in these portraits…Trent and Kaylee have that newly-engaged glow we can’t resist capturing!

oahu proposal portrait
newly engaged
happy couple
oahu proposal portrait
newly engaged

Trent and Kaylee met during the pandemic and, after many adventures, knew they wanted to spend the rest of their lives together. “She means the world to me. I am so excited to capture this moment for the two of us to cherish,” Trent told us before their Oahu proposal portrait session. How sweet is that?!

oahu proposal portrait
happy couple
oahu proposal portrait
oahu proposal portrait
newly engaged
oahu proposal portrait

Congratulations, Trent and Kaylee! We are so honored to be a part of this special moment! Mahalo and aloha from all of us at Karma Hill Photography!


Time Of Day: Sunset

Oahu Proposal Photographer: Megan of Karma Hill Photography

Oahu Portrait Location: Waimanalo Beach

Love the look of this Oahu proposal portrait? We think you’ll enjoy these ones on our blog!

Karma Hill - Hawaii
Owner | Website

Karma Hill is the owner of Karma Hill Photography, Simple Maui Wedding, Simple Oahu Wedding, and Simple Hawaii Wedding, marking a significant presence in the Hawaii wedding community since 2007. With a wealth of experience and a vast collection of informative posts on weddings and photography in Hawaii, Karma Hill offers unparalleled expertise. Explore the world of photography and wedding planning across Hawaii by visiting Karma's websites.

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