Henry, recently divorced, met Anna Ione Murphy in June, 1889 and married her in October, 1889. He was 43 and she was 19. She had moved to Oklahoma with her family who lived in an apartment in one of Henry’s six row houses on Grand. After their marriage they lived in Overholser’s Grand Avenue Hotel until they moved into the mansion on 15th Street in 1903. Their son Henry Samuel, born in 1890, died at 8 months of age. It wasn’t until 1905 that they would have a second child, a daughter named Henry Ione. A prominent hostess, Anna was also involved in the formation and growth of many social organizations including the Modern Classics Club, the Ladies Music Club, the Art League, the Republican Women’s Club, and the YWCA. She co-founded the Chafing Dish Society in 1899. Henry Overholser suffered a stroke in 1911 which left him partially paralyzed and wheelchair bound. He died in 1915. Anna lived in their house until her death in 1940.