The identification on the reverse includes a faded penciled "Luther and Nan" which has been over written with a typed "Mr. Luther Milstead and Miss Nan Simms, San Antonio Texas, Aug 09".
The most likely match for the man is Madison Luther Milstead, born February 18, 1883, in Madisonville, Texas, who by the time of the 1900 census is living in Tyler County, Texas, in central east Texas. Luther's death certificate gives his parents as Allen Milstead and Martha Risinger, but apparently his father either died or is out of the picture when Luther is still quite young. In 1900 his mother has remarried to Francis Marion Bass and the census tells us that they have been married since about 1886 and have at least five children of their own.
I was unable to find Luther in 1910, but I did find his WWI draft registration of 1918. That shows him living in Kirbyville, Texas, and working as a drug clerk in Orange. His nearest relative is given as Mrs. M. E. Bass (mother) and his description as medium height, medium build, brown eyes, black hair and with the history of a fractured arm.
Two years later, the 1920 census shows him living in Beaumont, Texas, still a drug salesman, boarding in the home of Joseph McKenzie. Luther has with him a new wife, Louise Barbin, who he married on December 31, 1919. In 1930 I was unable to find the couple, but in 1940 they are living in Port Arthur and Luther has become a collector for a retail clothing store. I never find any mention of children born to the couple. The last record I find for him before his death is his WWII draft registration, confirming his birthplace of Madisonville and showing his employment at that time with the Jefferson County Food Stamp Plan in Port Arthur.
Luther died on December 24, 1963, in Beaumont, after falling from his back porch, fracturing his left hip and ultimately dying from a pulmonary aneurysm. His occupation is given as collector for White House Dry Goods, and the informant is his wife Louise. He is buried in the City Cemetery in Kirbyville.
Louise survived her husband by nine years before dying on February 26, 1970. She is buried in the Forest Lawn Memorial Park in Beaumont.
Shifting to Nan Simms, I think I may have found the right woman in a Nancy Simms who is living in San Antonio in 1910. There is a photo of Nancy Simms attached to a public family tree in Ancestry, taken when she is middle-aged with grandchildren, and the eyes and cheeks are the same as the young woman in this photo.
Nancy Simms was born June 23, 1888, to parents Thomas and Josephine (Dunn) Simms. Thomas was a traveling salesman, making me wonder if he was a colleague of Luther Milstead. She married Lawrence Bartholomew Walker on June 5, 1912, and they had several children. She died on April 27, 1962, in San Antonio, and is buried in Chapel Hill Memorial Garden. Her obituary is found in the San Antonio Express-News and tells us she had one son and three daughters and at the time of her death 10 grandchildren.
This photo catches Luther and Nan in the prime of youth, before marriage and children and wars. A happy couple on a summer's day in 1909 in San Antonio.