 During leave in Staunton, Virginia in 1761, Fleming met Anne Christian (1744–1810), daughter of Col. Israel Christian (a wealthy landowner and the county's representative in the Virginia House of Burgesses) and his wife Elizabeth Starke.They married in 1763 and soon agreed to care for George Helvick, a three-year-old orphan.Their first son would be named Leonard Israel Fleming to honor his grandfathers.