Craig and Amber

Wedding Proposal Ideas in Kawaa, Hawaii

How We Met

Amber and I were matched online on Christmas Day with the help of eHarmony. Amber was apprehensive of the whole online dating experience, but thankfully her sister-in-law had been encouraging her to try it while she was home for the holidays. Apparently they both screened my profile and approved. Even after just a few emails, I could tell that she was a very sincere, thoughtful, and unique person. After we both returned from our Christmas breaks, we decided to meet up in DC. I had the most comfortable, enjoyable, exciting, and promising first date that I can remember and really hoped that she felt it too. Luckily she had a good time too and agreed to a second date a couple days later. We had been texting and talking quite a bit, so even before the second date, she had mentioned some weekend plans that were clearly not her first choice; I saw this opportunity and invited her for a hike to a very impressive waterfall nearby – the third date was planned even before we went on the second date, so that was clearly a good sign for me. The first two dates were me trying to impress her by being cultured and taking advantage of what the city has to offer – portrait gallery and then poetry open mic. The hike was a good test to see that she was a good sport (it was chilly) and also see that she was athletic. It was clear that we had a strong connection early on and were on the same page. Lots of people keep their options open early on when dating and see multiple people before becoming exclusive; thankfully this was not the case for either of us and we both preferred focusing on a single person entirely and were interested to see where this would take us.

Where to Propose in Kawaa, Hawaii

How He Asked

It was very clear to both of us that this relationship was not like any other we had been in. There were so many shared interests, values, respect, honesty, admiration, attraction, and other inexplicable pieces that made this complete. We joked about Amber breaking her lease early to move in, but as time went on, it made more and more sense, so she did and both were very happy for that decision. The year of being together had been fantastic with lots of adventures and things continued to improve, so it was clear to me that this is something I wanted for the rest of my life and that we were committed to making it work through whatever would come our way.

Craig and Amber's Engagement in Kawaa, Hawaii

I had a work trip planned for support in Pearl Harbor, Hawaii in March and Amber had talked about joining me. I had two weeks of work scheduled, so we booked her flight to meet me midway through the second week and then added some personal time to the end of that. I had big plans for the trip, but did my best to keep it a secret. I had a couple ideas in mind for how I would propose in Hawaii – I wanted it to be somewhere with a majestic view and also intimate. Everywhere you turn in Hawaii is gorgeous, but keeping away from the tourists to make it private was going to be a challenge. After a lot of research online, I found what looked like the perfect place – Crouching Lion trail on the Eastern side of Oahu. It was a short but challenging hike to a nice lookout over Kahana Bay. The only problem is that the trail is officially closed because of a couple unfortunate deaths in the last few years on the narrow, steep trail. The combination of this plus being on away from most of the tourist areas made me think that this could be fairly intimate as well. I started planting the seed early and told her how a friend of mine had recommended this hike and also some other hikes (didn’t want her to focus too much on this place and get suspicious).

Not content with just the natural beauty of this place, I figured I’d take it one step further and go for a sunrise hike since this was on the East side of the island. I had the first weekend to myself before Amber arrived, so I used this as an opportunity to scout out the location on my own. Arriving 30 minutes before sunrise, I was able to find the trailhead (marked with a trail closed sign) and climbed up the steep hills, pulling myself up on mangrove roots in one hand and my cellphone lighting the way in my other. I made it up and it was everything I hoped for, so I stayed up there for an hour deciding on the best location where we could have it to ourselves and still enjoy the view. There was a small flat rock that was away from the main lookout of the trail so it should be clear enough even if there were a few people climbing that faithful morning.

Sunrise on my scouting trip for the spot made it clear that this was an amazing spot:

I pushed my coworkers hard to finish the installation quickly so that the second week would be smooth and not too busy after hours. Amber arrived on Wednesday afternoon. By an amazing coincidence, Amber’s favorite band, Incubus, was playing at a very initimate venue in Honolulu that Thursday, so we had bought tickets and enjoyed a great show with them. I knew I wanted to do it on Friday or Saturday morning, but thought Friday would be better since there would likely be fewer people hiking that day. Luckily we were able to finish most of our work early and only had a wrap-up meeting on Friday around lunchtime, so that opened up the day nicely. Amber had only been in Hawaii two days so she was still mostly on Eastern time (six hours ahead), so it wasn’t too unreasonable to be up in time for a sunrise hike on Friday morning. We both woke up slowly, but decided it would be fun to go for a hike (I tried not to act too eager and excited, but could barely hold my excitement). We arrived at used our LED headlights to climb up the dark trail (I had suggested ordering these after seeing how dark it was the previous weekend). When we got to the top, I made sure we made a right turn away from the main lookout by telling her that I read about a better view that way. My desired rock was open so we made our way there. There was one other couple up there not too far away. They were taking sunrise pics as well, so I asked if they wouldn’t mind taking some pictures of us and they ended up taking some remarkable shots. If this hadn’t worked out, I had my tripod in my backpack, but would definitely not have been as great as their shots came out:

Not too much longer, the other couple moved on and headed back down so we had the place to ourselves. We enjoyed the beauty of the site and reminisced on how wonderful our relationship has been and how happy we both were. Amber made a mention of how she wanted to remember this place forever, so that was an easy opportunity for me to ask for her hand in marriage. I can’t remember exactly what I said, but I remember fumbling through my pocket trying to carefully pull out the ring that I had clipped in my pocket to a carabineer so that I wouldn’t drop it on the hike. Admittedly I didn’t drop to one knee, but that was only because I was so nervous that I didn’t think that would be a good idea on a trail that was only a few feet wide and already precarious. Amber immediately realized what was happening and cried happy tears and said yes. We stayed on top of the lookout for another half hour enjoying the moment and not wanting to ever lose that feeling. After many more pictures to celebrate, we made our way back down. We had three more days in Oahu and then four days in Kauai to celebrate as sort of a pre-honeymoon and had a wonderful time and a lifelong memory of that magical place. In planning for this, I had talked to my brother about this idea and possible hike, which he aptly named “Crouching Lion, Hidden Ring”.