Jonathan had planned for months to propose to my sister Cali while we were in Hawaii for Jenny, our cousin, and Archie's wedding. He vaguely knew he wanted to pop the question on the beach and so he enlisted my help the night before we left (in which I practically tripped over myself in shock and excitement with the news).
The only problem with that idea was Don, Jenny's brother, had also planned to propose to his longtime girlfriend Anna on the beach the next day as well (he had no idea of the coincidence by the way). While Jonathan and I both freaked out internally after he shared the news, Cali was oblivious to our distress and happily teased Jonathan about when he was going to pop the question himself. You can imagine the anxiety he was going through (and yes, I was just a tad bit sadistically amused at this predicament).
Because Don's plan involved a tucked away treasure chest full of memorabilia (including the engagement ring hidden in a seashell) set at a beachfront sunrise — aka, a comparably much more elaborate and meticulously thought out proposal — Jonathan chose to improvise something that day instead.
When he had asked me to help him out, we agreed that our signal of choice would be a wink. Between hiking at Diamond Head, snorkeling at Hanauma Bay, and hiking once again at Mariner's Bridge; I thought I was going to develop a broken neck with the amount of times I'd snap my head back at him for any indication of when he was going to whip out the ring.
It was only in the middle of our trek up Mariner's Bridge, while Cali was beasting it out ahead of us, that I caught his attention and pointed up in question, to which he discreetly nodded. At that point, even though every large rock resembling a makeshift chair seemed like a divine, torturous tease on my tired legs, I held on through with the knowledge of what was to come when we reached the top.
Once we did, we admired the vast view around us while fearing for our lives, as Cali defied gravity by dangling her legs over the cliff and taking selfies. Only after much protest and possible overreaction from Jonathan and me, she reluctantly moved to safer grounds.
Wanting a fuller picture of them and the view, Jonathan asked Don and me to take photos from an adjacent cliff. Thinking nothing of it, we headed over to do so. As we snapped away with our respective cameras, we saw from a distance a little shuffling and then suddenly, Jonathan was down on one knee! Luckily Don took as many photos as possible as the proposal unfolded, but once we saw them hugging, we both rushed over to the couple with congratulations.
Cali was happily crying as she released her arms from around Jonathan while I grinned from ear to ear. In between trying to wipe her eyes of tears, she kept glancing down at her ring in utter elation and disbelief. Don and I grilled them on what happened exactly, while I gave an accusatory glare at Jonathan for having not winked at me, and it was adorable to see the newly engaged couple stumbling over their words as they reenacted the scene.
Apparently Jonathan had kept the engagement ring inside his sunglasses case and asked Cali if she could put his sunglasses away. She was actually getting frustrated at him because she was trying to keep an eye out for me on the other cliff, but Jonathan kept on insisting that she retrieve his case. Angrily, she popped it open, saw the ring, and immediately bursted into tears.
Jonathan got down on one knee, asked the question, and in his nervousness, slipped the ring on her finger before she even said yes. Because she was covering her crying face, she didn't even realize it was already a done deal before they embraced each other and kissed.
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