The little girl in these photos is Eugenie Evelyn Jackson (1930-1998), the stepdaughter of a paternal third cousin, once removed, Eugenius Nesbit Freeman Jr.* who married her mother in 1936. School and newspaper records for Eugenie and her older sister Jessie show that they commonly used the Freeman surname but gave their correct maiden name when they got married.
I've identified the car as a 1932 Plymouth Coupe (note the rumble seat) and Eugenie looks to be about four so the photo dates to about 1934/35 and may have belonged to her birth father John I. Jackson.
According to the relative who posted these pictures, Gladys was the name of Eugenie's doll.
[Both photos shared to one of her public Ancestry.com family trees by agadobetty]
*As far as I can tell, E.N. Freeman (as he preferred to be known) never had any children of his own.
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