Herman Frederick Wilkening was my paternal great grandfather.

Herman was born July of 1865 in Chicago, Illinois. He worked for the Pennsylvania Railroad as a car inspector.

He first married Marie (Minnie) Sedvert  O'Malley in 1893.  Minnie was a widow with four children, Charles, Matilda,  Anne, and Edward by her first husband, Mr. O'Malley.
Herman and Minnie had four more daughters, Wilamina Johanna, Pauline, Bertha and Elsie Amelia.

Herman's second wife was Bertha. They divorced.

Herman married Mary Cottay (Aunt Mayme) on April 28, 1917, Cook Co, IL.
(Mary Cottay was a sister of Herman's son-in-law, George Cottay)

They had one son, Henry (Harry).

Herman died on the 24th of May, 1950.

Sources
1-1900 US Federal Census
2-Cook County, Illinois Marriage Index, 1912-1942