Darwin & Roland met online. They later found out that they both attended Aiea High School and in fact graduated one year apart from each other. They didn't really know each other during high school though Roland claimed that he knew of Darwin; though he thought his name was Dwight. Darwin and Roland met during the height of the Pokemon Go craze so surprisingly bonded while driving around town collecting items, battling in raids, and catching pokemon. They enjoyed attending zumba classes together as well as hiking at local trails. The two bonded over lip syncing over popular songs while driving, being fans of anything Disney, and eventually challenging each other in pickleball.

The plan to propose was months in the making. After finally deciding to take a leap of faith and propose, Darwin wanted ensure that the moment would be special; a Hallmark moment that he always wanted. Coincidentally, Darwin and his friends were already planning a trip to Disneyworld. In the months after his sister's wedding, Darwin felt that it would be the perfect time to pop the question. The months prior to the trip was spent trying to find the right ring (with the right fit!) and figuring out the timeline of events that would lead to the proposal, all while trying to keep the secret from Roland. Darwin recruited his friend (and now Best Man), Jared, to help with the set up and recording of the proposal. Although scared out of his mind, Darwin was still excited and already started telling some of his coworkers of his plans. It was the week of the proposal and we all safely made it to Orlando. After spending the first few days of the trip enjoying the Disney parks, it was time. The proposal was to be done at the Magic Kingdom during its 50th anniversary celebration fireworks show, "Enchantment." During the day Darwin and Roland "split up" with their friends to explore different parts of the park at their leisure. In actuality, Jared and his wife, Shawnie, took the time to get a Mickey Mouse ears hat and had it embroidered to memorialize the event. Later they asked Disney cast members to make the moment extra magical by finding us an isolated area away from the crowds. Darwin already booked a dessert party after the fireworks show that already separated them from the main crowd, however the Disney cast members pulled extra strings and secured an even more isolated area for us, right in front of Cinderella's castle. It was finally time for the proposal. Darwin and Roland met up with Jared and Shawnie and were escorted by cast members to a taped off area of the viewing garden for the fireworks show. Apparently Roland didn't stop to think of why we would be in a separate area away from other guests. There were already close calls where Darwin and his friends thought Roland might have figured out something was in the works. Luckily Roland later reported that he had no idea there was a plan to propose. Darwin nervously and quietly tried to ensure everything was in order before the show. Jared had to take Darwin away for a bit to keep his composure; he was starting to panic. Prior to arriving in Orlando Darwin watched the fireworks show online to time out when he would ask the question. The moment was practiced repeatedly in his mind but it was finally time to bring it to fruition. The fireworks show began, it was magical. Avid Disney fans, the music alone made Darwin and Roland emotional. However Darwin was starting to tear up for other reasons. The music cue was coming up. Darwin turned around to see his friends with cameras in hand. Darwin turned to hold Roland's hand. It was time. The finale of "Enchantment" reminded those who watch that we have the power to make our dreams come true. That "you are the magic." The music was at its climax and the final fire works were about to launch. Darwin put Roland's camera down and pulled him to his proposal spot (we were a few steps away from our ideal camera angle, lol). He went down on one knee with the fireworks around them and asked the most important question of his life. The words might have come out as mumbled nonsense as Darwin was already crying of nerves and time was running out for the show. Either way, Roland understood what was happening and said yes!!! It was as if everything happened the way it was supposed to be, a true Hallmark moment. After 5 years of being together, Darwin and Roland were finally engaged.