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Neither Greg nor Sydney can pinpoint the exact time they first met. They both attended college at the University of North Carolina's Asheville campus - Sydney started as a freshman and Greg as a transfer from North Georgia College. During their first few years at UNCA, Greg and Sydney saw each other around campus and at various parties enough to know that the other existed, but they were in different social circles and never formally met. Once senior year started in 2013, their two friend groups began to merge and Sydney caught Greg’s eye for the first time. Greg remembers the moment he noticed Sydney and immediately asked a mutual friend whether or not she was in a relationship. The answer, of course, was that she was in a long-term relationship and phrases like "out of your league" and "keep dreaming" filled the rest of the conversation. A few months later, however, Greg heard that Sydney's long-term relationship had ended. Greg was devastated to hear this and began pursuing Sydney immediately. It started out slow during their final semester of college, but their relationship had an expiration date. Before they started dating, Greg had already purchased a one way plane ticket to South America with plans to leave immediately after graduation and travel indefinitely. By the time they graduated, however, Greg had shortened the trip to a 3-month itinerary and purchased a second ticket. After dating for only 3 months, Greg and Sydney took off for a 3-month backpacking trip throughout Columbia, Ecuador, and Peru. That trip set the tone for their relationship and, 9-years later, their adventure continues.

On Friday April 1st, 2022, Greg woke Sydney up at 2am and asked her to get ready for a flight - she would not be going to work that day. This was confusing for Sydney, not only because it was crazy but because she had a big meeting that Greg had watched her prepare for all day the day before. She kindly asked him to stop speaking to her and tried to go back to sleep. Greg finally got her out of bed letting her know that everyone at work was aware, and he had already packed most of her things. He gave no details of where they were going, so it wasn’t until their layover in Denver that Sydney saw their final destination of Durango, CO. They spent the day walking around the area, and on Saturday morning he surprised her again by driving them down to Silverton, CO, a place they had visited on their road trip out West 5 years earlier. They had all their snowboarding gear so she assumed they were going to some sort of ski resort though she did not know of any in Silverton. When they arrived at their destination there was only one lift and a small shack where people were lining up. In the shack they handed over a waiver for them to sign, and Sydney realized for the first time that they would be going HELI SKIING. After the 2nd time of reaching the top of the mountain via helicopter, Greg got on one knee and asked her to marry him.