In 1794, Washington wanted to find a way to avoid war with both countries. He appointed his fellow Virginian James Monroe as his ambassador to France. Since 1790, Monroe had been the US Senator from Virginia. After the death of Senator William Grayson in 1790, Monroe was elected to serve the remainder of Grayson's term. Monroe resigned from the senate to accept the post in France. To create a balance among the competing interests, Washington appointed Federalist John Jay as his Ambassador to the United Kingdom.
Monroe sailed for France, and took up residence in Paris. After arriving in France, Monroe addressed the National Convention, the third government of the French Revolution. He gave a speech celebrating republicanism, and received a standing ovation, but back home, it was something that Washington was not pleased about. Washington wanted to maintain a position of neutrality and was displeased by Monroe's support for the French while representing his government.
Monroe experienced several early diplomatic successes. He successfully negotiated the protection of U.S. trade from French attacks. He also used his influence to win the release of Thomas Paine and Adrienne de La Fayette, the wife of the Marquis de Lafayette. Paine was arrested in France on December 28, 1793. Paine protested and claimed that he was a citizen of the U.S., which was an ally of Revolutionary France. Gouverneur Morris, who had been the American minister to France prior to Monroe, did not support this claim, and Paine later wrote that Morris had connived at his imprisonment. Paine narrowly escaped execution his jailer left a chalk mark in the wrong place, that was supposed to show that the prisoner inside was due for execution. Paine was released in November 1794 because Monroe successfully argued the case for Paine's American citizenship. The French government were more receptive to Monroe's pleas, after Monroe's favorable address to the Convention.
After France declared was on Austria on April 20, 1792, the Marquis de Lafayette left for command of the army at Metz. After returning to Paris to defend the King, he was accused of treason, and sought to escape to the Dutch Republic, but was arrested on August 19 by the Prussians at Rochefort, Belgium, and imprisoned at Magdeburg, Prussia. On September 10, 1792, his wife, Adrienne, was held under house arrest at Chavaniac. In May 1794, during the Reign of Terror, she was transferred to La Force Prison in Paris. Her grandmother, Catherine de Cossé-Brissac duchesse de Noailles, her mother, Henriette-Anne-Louise d'Aguesseau, duchesse d'Ayen, and sister, Anne Jeanne Baptiste Louise vicomtesse d'Ayen, all met their death by guillotine on July 22, 1794. Adrienne was transferred to the Collège du Plessis prison, then to a house on rue des Amandiers, then to the Desnos house, rue Notre-Dame des Champs. But on Januart 22, 1795, she was released due to the efforts of James Monroe and his wife Elizabeth, who visited Adrienne in jail. On September 1, 1795, Monroe issued Adrienne American passports for her and for her children. They had been granted American citizenship. Adrienne traveled to her husband's place of imprisonment. In April 1795, her son Georges was sent to America, where he studied at Harvard, and stayed with George Washington.
After Monroe arrived in France, the U.S. and Great Britain concluded the Jay Treaty. The treaty outraged both the French and the Republicans. Monroe had not been fully informed about the treaty prior to its publication. He was tasked with repairing the rift caused by the treaty in US-French relations. Monroe had some success in what was probably an impossible task. He was able to successfully negotiate U.S. navigational rights on the Mississippi River. The mouth of the river was controlled by Spain, and in 1795 the U.S. and Spain signed Pinckney's Treaty. The treaty granted the U.S. limited rights to use the port of New Orleans.
Washington was unhappy with Monroe's inability to convince the French of the benign nature of the Jay Treaty, and generally with Monroe's failure to project a posture of neutrality. Washington recalled Monroe from his post in November 1796. Monroe returned to the United States, where he wrote a 400-page defense of his tenure as ambassador. In the report he was critical of Washington's desire to pursue closer relations with Britain at the expense of relations with France. Monroe became a member of the Democratic-Republican Party, a political party organized by Jefferson in opposition to the Federalists. He returned to his home in Charlottesville, where he resumed his dual careers as a farmer and lawyer. Three years later in 1799 he was elected Governor of Virginia.
In 1800 Thomas Jefferson was elected President. Jefferson sent Monroe back to France to assist Ambassador Robert R. Livingston in negotiating the Louisiana Purchase. In the 1800 Treaty of San Ildefonso, France had acquired the territory of Louisiana from Spain. Many in the U.S. mistakenly believed that France had also acquired West Florida in the same treaty. The American delegation wanted to acquire West Florida and the city of New Orleans, because it controlled the trade of the Mississippi River. Jefferson wanted to acquire New Orleans. He authorized Monroe to form an alliance with the British if the French refused to sell the city.
Monroe and Livingston met with François Barbé-Marbois, the French foreign minister. They agreed to purchase the entire territory of Louisiana for $15 million in what became known as the Louisiana Purchase. In agreeing to the purchase, Monroe exceeded his instructions, which had only allowed him only to agree to pay $9 million for the purchase of New Orleans and West Florida. The French did not acknowledge that West Florida remained in Spanish possession, and the United States would claim that France had included West Florida in the sale. Jefferson approved of Monroe's actions, which ensured that the United States would continue to expand to the West. Ignoring and doubts about whether the Constitution authorized the purchase of foreign territory, Jefferson won congressional approval for the Louisiana Purchase, and the acquisition doubled the size of the United States.
Monroe traveled to Spain in 1805 to try to win the cession of West Florida, but, with the support of France, Spain refused to consider relinquishing the territory.
Monroe was appointed as the ambassador to Great Britain in 1803, following the resignation of Rufus King from the post. The major issue of contention between the United States and Britain was that of the impressment of U.S. sailors. Many U.S. merchant ships employed British seamen who had deserted or dodged conscription, and the British frequently impressed sailors on U.S. ships in order to recapture deserters and to replenish their supply of sailors. But many of the sailors they impressed had never been British subjects, and Monroe was given the job of trying to persuading the British to stop this practice. Monroe was unsuccessful in this task, largely due to Jefferson's alienation of the British minister to the United States, Anthony Merry. Monroe was offered the post of serving as the first governor of Louisiana Territory, but he refused. Instead he continued to serve as ambassador to Britain until 1807.
In 1806 Monroe negotiated the Monroe–Pinkney Treaty with Great Britain. It would have extended the Jay Treaty of 1794 which had expired after ten years. Jefferson had opposed the Jay Treaty, but it had produced ten years of peace and highly lucrative trade for American merchants. When Monroe and the British signed the new treaty in December 1806, Jefferson refused to submit it to the Senate for ratification. The treaty called for ten more years of trade between the United States and the British Empire, but Jefferson was unhappy that it did not end the practice of impressment. Jefferson made no attempt to obtain another treaty, and as a result, the two nations drifted from peace toward the War of 1812. Monroe was unhappy about the administration's repudiation of the treaty. He returned home to Virgina in 1807.