Isaac and Natalie met on Hinge (online dating app) on August 6th, 2024. They initially matched while talking about backpacking and their faith. They exchanged countless paragraph texts over the next week. A week after matching, they went on their first date at Kenilworth Park. They spent the next two hours walking and bonding over backpacking gear. Over the next few months, Isaac and Natalie went on many hikes and adventures and grew closer together. Through discussions of their faith and values, along with obvious chemistry, it was clear to both of them early on in the dating process that this relationship would lead to marriage.

Natalie and Isaac got engaged on June 7th, 2025 on the Appalachian Trail during their first backpacking trip together. They planned to go backpacking with Natalie's sister and brother-in-law five months prior to the trip, and Isaac was already thinking that this would be the trip to propose to Natalie. As much as Isaac was trying to keep the exact timing and location of the proposal a surprise, Natalie had a strong hunch that the engagement would be happening on the trip (Natalie here, there were lots of clues and plenty of engagement discussion before this trip). The time came with the trip planned. With the ring stowed in his hip belt, they started their two-day overnight trip on the trail starting from Port Clinton, completing 6.5 miles the first day. After a restless and muggy night sleeping at the Windsor Furnace Shelter, they woke up (or rather opened their eyes) and started back on the trail at 7 am. About 2 miles into the hike they arrived at Pulpit Rock. Two trail runners were just leaving the vista and after some additional stalling from some nerves, Isaac brought Natalie out on the rock, got on one knee and proposed to Natalie (obviously she said yes, and Isaac already knew what her answer would be) (kudos to Alec Smith for capturing the proposal picture). They hiked 17 more miles to finish up that section of the Appalachian Trail... And then proceeded to go to Red Robin with Marley and Alec and drop $134 on burgers, fries, and milkshakes.