Jackson and Grace met while standing in a three-hour line at The Broadway in South Boston on the day the mask mandate was lifted in May 2021. After speaking for about ten minutes, nothing came from the encounter except for Jackson thinking Grace was "cute." Months later, in August, a mutual friend mentioned to Grace that Jackson wanted to take her on a date. A couple of days passed before Grace decided to confidently slide into Jackson's DMs with, "I heard you’re taking me on a date," to which he replied, "News to me, but I'm into it." After their first date, the two have been pretty much inseparable.