Stephen was attending a birthday dinner for his friend and future groomsmen, Mark Clements, when he was introduced to Mark's friend Briana who just so happens to be Mai's boss at the hospital. He must of made a good impression on her because shortly after that evening Briana decided to play matchmaker. She told Mai about the guy from the Birthday dinner and then she contacted Stephen and told him about her co-worker. Stephen asked Mai on an unconventional breakfast date at a local spot and the two of them hit it off, despite a few nervous first date jitters. The two of them had such a great time that they decided to meet up again that evening for date number two. That same month Covid ravaged the world and lockdowns were implemented. With businesses and gyms closed Stephen and Mai had to get creative and their future dates consisted of traveling around the state, hiking up every peak they could find with their newly adopted pup RZA.

Stephen proposed to Mai on their last day of vacation in Key West, FL while stargazing on the beach.