Gregory and Sheena met while working together at Windsor High School. Gregory tried, unsuccessfully, to capture Sheena's heart for a full year. Stopping by her classroom, conveniently needing the copier at the same time, even having the desks next to one another in the office, yet no dice for Gregory. However after a night of a few drinks, a terribly played game of pool, and an argument about rappers Kanye West and Drake at a staff event at Windsor's infamous Tobacco Shed, Gregory finally won her over. Eight years, two kids, and a condo later here they are ready to make it official!