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Dolley Madison almost fits this description - she was a widow of age 26 who had married at 18 when she married James Madison, but she had only one young son.

Sorry J.P. Helm, but your answer is incorrect for this question. Martha Dandridge was 18 years old when she wed Daniel Parke Custis in 1749. Although they produced four children, two of the children, along with her husband, had died by 1757 when she was 26. At age 28, Martha then wed Colonel George Washington and had no more children.

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Q: Which first lady was originally married at 18 and became a widow with two infants by 26 and married a future US president at 28?
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