Jonathan was likely the oldest son of Joseph Bennett Sr., based on his precedence in the will of his father. His year of birth is an estimate based on his younger brothers. He grew up on Joseph's tobacco plantation in southern Virginia, near the present day town of La Crosse.
Per the book "Mecklenburg County Marriages, 1765-1810", Jonathan Bennett married Sarah Tanner on December 17, 1793. Thomas Tanner served as surety.
Jonathan was named as executor for his father's will in 1805, along with his brother William. In the terms of the will Jonathan was left five slaves, half of the land where Joseph Sr. lived, on half of the land purchased from Anthony in 1796, and one half of his mill.
Per Jonathan Bennett's will filed December 1825, from Mecklenburg county will book #11 page 117, he left one half of his land to his son, Jonathan. He left the other half "to my daughters, to be equally divided". He also divided his slaves among the children. He directed that his interest in "the milll of Bennett and Watson" to be sold.
Jonathan names one son in his will, also named Jonathan, and references a plural number of unnamed daughters. From unverified online sources, the children of Jonathan and Sarah were likely:
Jonathan H. Bennett (b.? d.?)
Jane (b.? d.?)
Sally (b.? d.?)
Martha (b.? d.?)
Elizabeth (b.? d.?)
Rebecca (b.? d.?)