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Jonathan Jennings
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===Courtship and marriage=== During his first session in Congress, Jennings had a small portrait of himself made, which he later gave to Ann Gilmore Hay, the daughter of a prominent Charlestown politician, whom he had recently begun courting.<ref group = n>The painting is the only known authentic portrait of Jennings. Both of Jennings's official portraits are based his 1809 portrait. See Mills, p. 133.</ref><ref>Gugan and St. Clair, p. 42</ref><ref>Riker, p. 231</ref> Hay was born in Harrodsburg, Kentucky, in 1792. Her family moved to Clark County in Indiana Territory, and settled in Charlestown. Jennings first met her when he was campaigning for Congress in 1809.<ref>Mills, p. 132</ref> After his first session in Congress ended, Jennings returned to Indiana Territory and married eighteen-year-old Ann on August 8, 1811.<ref name=r232>Riker, p. 232</ref> Ann's father had just died leaving her with no family or means of support.<ref>Mills, p. 133</ref> Following his reelection to Congress in 1811, the couple returned to Washington, where she remained briefly, before traveling to Pennsylvania to live with Jennings's sister, Ann Mitchell, for the remainder of the session.<ref>Mills, p. 136</ref> Jennings's wife suffered from ill health, which deteriorated after he became governor of Indiana in 1816, and she died after a protracted illness in 1826.<ref>Mills, p. 175</ref> Later that year Jennings married Clarissa Barbee, who had come from Kentucky to teach at the Charlestown seminary.<ref name=r237/><ref name="Mills, p. 219">Mills, p. 219</ref> Jennings had no children from either marriage.<ref name=w41>Woolen, p. 41</ref><ref>Mills, pp. 209-210</ref>
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