When Joe reached out to us, he had a plan, a brilliant, heartwarming, sneaky little plan. He told Leilani they were just taking couples portraits on their Hawaii vacation. A fun photo session, nothing out of the ordinary. But hidden behind the casual smiles and hand-holding on the itinerary? A ring and a once-in-a-lifetime surprise with an Oahu proposal portrait!
The setting? The breathtaking Papailoa Beach on Oahu’s North Shore, with golden light brushing the sand and waves tumbling in the background like applause. It was Leilani’s first time back to Hawaii in seven years, a place she grew up visiting, where her mom had lived, and where countless childhood memories were rooted. For Joe, this was his first time on the islands, making the moment all the more meaningful.
They met two and a half years ago during a blizzard in Chicago (because every great love story needs weather drama), and ever since that five-hour first date, they’ve been inseparable. Through travel, life, and raising their dog Kylo together, they built a life full of joy, and this Hawaii trip was something they’d talked about since the very beginning.
Ready to see if his plan worked? Just you wait!




So when Joe dropped to one knee, Leilani was not only picture-perfect, because of course she thought they were just doing a photoshoot, but completely, joyfully surprised. She said yes, of course!
We were honored to capture every second. The laughter, the tears, the look on Leilani’s face when she realized what was happening. It meant the world to them, and to us, to freeze this moment in time.

















Congratulations, Joe and Leilani. You started your Hawaii vacation in the most unforgettable way possible, and we’re so thrilled to have been a part of it! We hope you have a wonderful time exploring the island together as a newly engaged couple!
Let your next chapter begin!
Time Of Day: Sunset
Oahu Portrait Location: Papa’iloa Beach
Proposal Photographer In Oahu: Kelsey of Karma Hill Photography
There are few things more beautiful than a giant, joy-filled Big Island family portrait beach session… especially when it takes place on the ruggedly stunning shores of Old Kona Airport Beach. The Bogusch-McConnell crew showed up in full force, multiple generations, big smiles, sweet connections, and outfits in the dreamiest summery palette. And it was
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.