After seeing Greg perform at Rudy's Jazz Room in Nashville, TN on October 18th 2018, Jessie followed Greg on Instagram and they instantly became friends. A year later, she went to another one of his shows (with a date might I add), and on January 10, 2020 took him up on his long standing offer to be tour guide the next time she was visiting New York. The evening, accompanied by her bestie Gatlin and Gatlin's husband, included jazz clubs, the Friends apartment, and two hours of Scrabble. They both left the trip feeling excitement, peace, and joy about the weekend. Greg called Jessie two days after she returned to Nashville and said he wanted to "intentionally get to know her". She accepted and their dating relationship began (although Jessie believes it became official on March 15). They had a long-distance COVID relationship with Disney+ movie nights, writing Emergen-C jingles, and Zoom cooking sessions until Greg moved to Nashville in June to give their relationship a real shot. Clearly it has worked out. 2020 has been a challenging year and it has been a VERY good year for these two.