Bailey and Henry met at Plattekill Mountain, a ski mountain in Bailey's home town of Roxbury, NY. Henry had "his eye" on Bailey for months (possibly even years!) while skiing around the mountain. On the night of the annual ski patrol party in 2013, Henry finally built up the confidence to finally introduce himself to Bailey. He was pretty bold, saying "Hi Bailey" to which Bailey snapped back, "How the hell do you know my name?" Well, as you might have guessed, the night went much smoother following that rough introduction. If you ask them now, they pretty much made an instant connection. After riding the chairlift together that night for the annual torch light parade, they kindled a high school long-distance romance. Things were tough as young lovers who could not drive but lived one hour apart, Bailey from Roxbury and Henry from Cooperstown. They learned to make it work: skiing together on the weekends, begging family for rides in the off-season, and occasionally even taking the Oneonta Public Transport bus. After they got their driver’s licenses, things became much easier, or so they thought. High school ended and they headed off to college and Bailey eventually to medical school. It was a very rocky road and at times, it seemed like this high school romance would not last. However, as Bailey neared the end of medical school, she matched into residency in Portland, ME. Henry graciously decided to give up his EMS and 911 career in New York to make the move to Portland with Bailey. Honestly, residency tested their relationship more than they would ever expected with long work hours, the stress of new jobs, and being away from family. However, with some crying (mostly on Bailey's part) and a whole lot of laughing, they have learned to embrace the chaos together. They live in Westbrook, Maine with their three dogs, Dream, Zulu and Tilly, where they strive to be the best darn dog parents to their spoiled girl gang. When they are not working, they enjoy being "foodies: at all the awesome restaurants in Portland, taking the dogs on outdoor adventures, and still trying to squeeze in an occasional ski adventure!

Finally, after 12 years, Henry decided to start planning his proposal. After thinking about it for months, Henry decided to ask Bailey's parents for their permission to propose to their daughter. Getting the approval, both of them saying "Duh!", Henry began his engagement ring adventure. Keeping it quiet from Bailey was a task all in itself. Working together with Christy, Jason, and Jacey, he was able to keep the plan a total secret from Bailey for many months. Finally, the day came in mid-February 2022. Bailey went home from Maine to New York to ski and see her family. Henry snuck home the day after Bailey left, staying at a family friends house nearby. The next day, Henry arrived very early to the place they met, Plattekill Mountain. Henry waited in the top ski patrol shack for Bailey's arrival, surprising her at the top of the North Face. With the snow flying, Henry got down on one knee and asked her to marry him.