From President James Monroe to His Namesake Nephew: Advice on Courting and Love

James Monroe’s mother died in 1772, and his father two years later. Though he inherited property, including slaves, from both of his parents, the 16-year-old Monroe was forced to withdraw from school to support his younger brothers. He was therefore experienced in guiding and giving advice to youths. One of these brothers was Andrew Augustine Monroe, who married in the 1790s, and in 1799 named his only son after his brother – James. When in 1805 the elder James Monroe came into sole possession of his uncle’s valuable estate, he gave management of the estate to his brother Andrew, who lived at the 6-room overseer’s house from 1808 to 1817. James continued to feel responsibility for young family members, particularly so in James’s case, as the lad had little schooling and was ill-disciplined by his parents.

James Monroe the elder was U.S. Ambassador to France during the Napoleonic Era, and was governor of Virginia in 1811. But he left that year when, in April 1811, President James Madison appointed him Secretary of State in hopes of shoring up the support of the more radical factions of his Democratic-Republican Party. From 1814-1815, Monroe also served as Secretary of War. In 1816 Monroe was elected President of the United States, and took office on March 4, 1917. He served for eight years, a period known as the Era of Good Feelings.

At the young James’s desire, his powerful uncle had him appointed to the West Point Military Academy, from which he graduated in 1815. In the army, he served as aide-de-camp to General Winfield Scott. After that he moved to New York and became a politician, serving in Congress during the Van Buren administration. He hob-nabbed with the rich and prominent in the city, such as the Schermerhorns, and his grandson married Theodore Roosevelt’s sister (who was also the aunt of Eleanor Roosevelt).

Autograph letter signed as President, Washington, November 2, 1821, to James. In it, he gives James advice on visiting and helping his needy brother, and particularly how to proceed in his courtship of his future wife, Elizabeth Mary Douglas.

“If the Lady, with whom you have a particular relation in N. York, has not returned there, had you not better, avail yourself of the opportunity to go to Virginia to see your father & his [brother’s] family? There are many reasons why you should take that step, which merit your attention. First it will be gratifying to your parents, to whom you may give useful advice as to their own concerns. Secondly, it will enable you to confer freely with your brother, & to give him advice also which may be useful to him. I understood from your father, that one reason assigned by your brother, for doing nothing for himself, & making no exertion, was a suggestion from you, that he had better remain as he was, till you saw him. I suspect that you merely meant, that when you saw, you would give him your advice, but did not mean, to prevent his his exertions in the mean time.

“Another reason occurs in favor of this visit, which is that by withdrawing from N. York, till the Lady returns there, & for some time afterwards, on a visit here & to your father, it will be shown, that you do not rest your future prospects & hopes entirely on her, or her family. I think, the step would raise you in her estimation, & that of the family as well as of others. It might be advisable for you to leave no message to her, & even to leave her to doubt, whether you had not been justly wounded at her going into Canada, after promising not to go. That however should be left to inference only, & not the subject of a message, nor would I say so to any one, to report it to her.

“Hortensia [Monroe’s granddaughter] is still dangerously ill. Your aunt, accompanied by Mr. Hay [Monroe’s son-in-law], left this yesterday, for General Ringgold [a relation by marriage to Hay], to afford such consolation as circumstances may require, & she be equal to. Col. Lane has returned in a very low state, just recovered, so far, from a long & distressing fever. Your friend, James Monroe.”

Here we see Monroe contemplating maneuvers for his nephew to take to better position himself to be in the driver’s seat when dealing with his potential wife and her family.