This does not answer your question about Nathan, but are you sure Annie remarried. The Informant RL Glasscock, mentioned on FindaGrave might be the son Robert FL in the 1900 census?
Burial:
https://www.findagrave.com/cgi-bin/fg.cgi?page=gr&GSln=Glasscock&GSiman=1&GScid=2237&GRid=47595885&
Annie Gale Glasscock Glasscock
Birth: Jun. 13, 1871 Hebbardsville, Henderson, Kentucky
Death: Nov. 25, 1950 Italy, Ellis, Texas, USA
Information from Death Certificate:
Name: Annie Gale Glasscock
Death date: 25 Nov 1950
Death place: Route 1, Italy, Texas
Gender: Female
Race or color: White
Age at death: 79 years 5 months 12 days
Birth date: 13 Jun 1871
Birth place: Hebbardsville, Kentucky
Marital status: Widowed
Father name: Joe Lewis Glasscock
Father birth place: Kentucky
Occupation: Housewife
Residence: Italy, Ellis, Texas
Cemetery name: Bardwell Cemetery
Burial place: Bardwell, Texas
Burial date: 26 Nov 1950
Informant: R. L. Glasscock (her so
Death Record: "Texas Deaths and Burials, 1903-1973," database, FamilySearch (
https://familysearch.org/ark:/61903/1:1:F6T5-2Q1 : 12 December 2014), Annie Gale Glasscock, 25 Nov 1950; citing Italy, Ellis, Texas, reference v; FHL microfilm 1,711,211.