[1] Day was born in Palm Beach, Florida to Jim Hillegass and Linda Sapp.
Day is a 2000 graduate of Whitehall-Yearling High School in Whitehall, Ohio where she was raised by her mother and her stepfather Charles Boggs.
Day's grandfather is Bill Sapp, a central Ohio restaurateur who, with his partner Lee Henry, established The Top steakhouse, The Kahiki and The Wine Cellar restaurant in the 1950s and 1960s.
[2][3] She was successful after previously placing as a semi-finalist in the pageant in 2003, 2004 and 2006 and making the Top 5 at Miss Ohio Teen USA 2000 (under the name Monica Day-Boggs).
Day appears on WCMH 4, an NBC affiliate based in Columbus Ohio where she is an anchor for the morning news broadcast.