Alana and Jon first found each other on the Hinge dating app. Despite Jon's many fish pictures, Alana agreed to go on a date. A few hours after their first date, Jon woke up feeling terrible and tested positive for Covid and spent the rest of the night worrying if he would ever get a second date with Alana if he had given her Covid on their first. Luckily, it turned out that Alana had already survived her second bout of Covid a few weeks earlier. While their second date may have been delayed by the requisite quarantine period, Jon and Alana have never gone a single day without talking to or seeing each other in the three years since that first date.

Christmas day 2023, Jon and Alana left for a vacation to Hawaii. Jon knew he was going to propose but was torn between doing it during the waterfall landing of their helicopter tour, or later in the week during their sunset sailing trip. He finally decided on the sailing trip, with the tie breaker being Alana's love for beautiful sunset pictures. During the helicopter tour, he found himself second guessing if he had made the right decision because the waterfall site was so beautiful. The second guessing only increased the next day when hours before their sunset sailing trip, the captain called to say that due to mechanical issues the trip would have to be rescheduled or canceled. Luckily, Jon and Alana were able to reschedule for later that week. Jon spent the first half of the sailing trip nervously debating what would be the best moment to pop the question. The conditions were much more windy and wavy than anticipated and while Alana was below deck, the captain said he couldn't say whether conditions would get better or worse. So when Alana came back up and the sun was beginning to set, Jon suggested they walk out to the front of the boat for pictures. Alana was immediately a bit suspicious about Jon actually requesting to take pictures and thought she might know what was about to happen, but as soon as the deckhand put their favorite song on the stereo she knew exactly what Jon was about to ask. After lots of happy tears and a few glasses of champagne to celebrate, the perfect evening was capped off when on the return to the harbor, a whale surfaced near the boat and started repeatedly slapping it's tail on the water as if to wish "congratulations" to Jon and Alana.