Almost every one of young George Washington’s romantic interests is obscure. Martha Custis was a relatively late arrival in Washington’s love life, but with the exception of one other young woman, all those who preceded her are mysterious, the subjects of little more than veiled and sometimes cryptic exchanges between Washington and his friends.
There was, for instance, the son of a childhood friend who recalled his father telling stories about young Washington romping with a “large girl” in a schoolyard. At least one writer claimed he could identify the girl as Jane Strother, the daughter of a Stafford County neighbor during George’s youthful Fredericksburg days. Later, Washington thought a girl named Frances Alexander charming enough to compose an acrostic poem for her in which the first letter of each line spelled out her name vertically, though he only got as far as the second “a” in Alexander. One writer suggested that it wasn’t Frances Alexander at all, but someone named Frances from Alexandria. The paucity of material has forced biographers to ponder such questions.
Courtship consists in a number of quiet attentions, not so pointed as to alarm, nor so vague as not to be understood. — Lawrence Sterne
Around 1749, possibly 1750, when he was eighteen, Washington made a puzzling reference to a “Low Land Beauty” in a letter that itself has been a source of disagreement, specifically whether it was a letter at all or merely young Washington practicing letter writing. Nobody knows who the Low Land Beauty was, and the letter in question is merely an undated draft copy in a memorandum book that an editor surmised was written around 1749 or 1750 to someone named Robin, whom Washington calls a “dear friend.” The Low Land Beauty has been identified as Betsy Fauntleroy or Lucy Grymes or others, but only through the most casual detective work. This is proven in the case of Betsy by the fact that she would have been only twelve years old at the time. Lucy Grymes was old enough to be courted, but her name seems to have been just as conjectural. She married Henry Lee, was the mother of “Light Horse Harry” Lee, and Robert E. Lee’s grandmother.
Nobody knows who someone named “Nell” was. One of Washington’s friends described her in a way that suggests she was a prostitute or at least willing to act like one. Betsy Fauntleroy did eventually attract Washington’s attention when she was sixteen and he was twenty and by then was earning a bit of money as a surveyor. Betsy’s father, however, seems to have judged Washington’s prospects as too flimsy for him to sanction a courtship. The Fauntleroys were educated and prosperous Richmond County planters who likely considered themselves George’s betters, and in any case, Betsy did not find George appealing.
By 1756, Washington’s exploits as a militia officer fighting the French and Indians on the Virginia frontier were beginning to make him famous. The following year he made his first trip north, a journey to Boston that required him to stay in New York City along the way. Many of the details about this trip must be inferred, but he likely lodged with Beverley Robinson because his careful record of expenses doesn’t include entries for board and food. There he met Robinson’s sister-in-law, a twenty-six year old heiress named Mary Philipse. Beyond this concrete fact almost everything about this interlude has probably been exaggerated.
It is no exaggeration, though, to say that Robinson’s wife Susannah and her sister Mary, who went by the diminutive Polly, were rich: Polly owned more than 50,000 acres of prime real estate on the Hudson River, which was certainly enough to endear her to the most finicky suitor, and the dashing visitor from Virginia was not all that exacting. And Polly was not only wealthy but fetching, buxom with rosy cheeks that dimpled when she smiled, though her habit of wearing a choker suggests that she was trying to hide a touch of goiter. Her main flaw was a willfulness that made her bossy, something that could have reminded Washington of his mother, and even if he had been attracted to Polly, her imperious streak would have been a major impediment. During the Revolution, the Philipse women were steadfast Tories, and an idea of her personality can be taken from a remark made years afterward by her grandnephew. Responding to the observation that her fate would have been very different had she married George Washington, he said sharply that “she would have prevented” Washington from becoming “a traitor.”
Stories later claimed that Washington proposed to Polly Philipse. Perhaps he did. He did stay for the better part of three weeks in New York City as he went to and came from Boston, a long delay for a long trip. He took in the sights with female companions who are presumed to have been Susannah and Polly, including two outings to an exhibit of small mechanical toys arranged in dioramas under the title “The Microcosm, or World in Miniature.” But like much else in this episode, these events are gleaned from a few nondescript references in scattered letters and Washington’s account book. At this time in his life he could be impetuous and even imprudent about women, as other events would soon prove. But if he did ask Polly to marry him, she obviously said no. One story says she found his nose unattractive. Two years later she married Roger Morris, one of Washington’s fellow officers on the Virginia frontier.
All of these women — from the large girl in the playground to the New York heiress — seem to have been fleeting whimsies. Possibly they inspired immature affection that seemed at the time more serious than it was, which is normal for all young people finding their way. If the series of lost loves makes it seem that Washington was willing to pop the question at every opportunity, and that every girl spurned him, it is probably because we know so little about the women in his life during his youth. There is nothing to suggest, as some have, that his considerable height made him seem freakish to girls, or that his large hands put them off. Nor was he apparently awkward or stumbling in conversation. He was tall, fair, handsome, gave off an air of confidence, liked to dance, and by his mid-twenties was already being talked of as a military hero with a commanding presence. And yet, being in his mid-twenties made him something of an oddity in the marriage stakes of colonial Virginia. Given life expectancy, and especially for Washington men who were notoriously short-lived, someone pushing thirty in the mid-eighteenth century was entering middle age. Yet George Washington doesn’t seem to have pursued any particular girl with determination until 1758, which was when he began his brisk courtship of Martha Custis, a young widow with two children. (As we hint in the opening, there is a bit more to this story that we talk about in a special Valentine’s Day edition of our newsletter, “An American Album.”) Washington married Martha Custis in 1759.
As he grew older, moments of amusement were rare for this reserved man, but there is one event that suggests a different person from the aloof figure Americans picture when they think of George Washington. It possibly provides a window on his larkish behavior as a youth. It happened during the Revolutionary War when the army was in winter quarters at Morristown, New Jersey. For Washington, it turned out to be a rare instance of bad judgment that caused an awkward incident.
Nathanael Greene's deputy quartermaster, Colonel Clement Biddle, had brought on a Rhode Island accountant named George Olney to straighten out the department's ledgers. Biddle hosted a dancing party to welcome Olney and his wife Deborah.
Everybody was game. Nathanael Greene’s wife, a pert woman younger than he (she was in her mid-20s), had just given birth to their first child but had quickly regained her strength and figure and was ready for a festive night. Catharine was her name, but everyone called her Caty, and she could be volatile and jealous. She had developed a proprietary interest in Washington as a dancing partner. The previous season, before her baby, they had danced for almost three hours without interruption. At the time, Washington had made a winking joke that he was keeping Caty from her "Quaker Preacher.”
It was all in good fun, but the Biddle gathering disappointed Caty Greene. In an effort to make a newcomer feel welcome, Washington paid too much attention to Deborah Olney, and George Olney was a teetotaler, something he seemed unduly proud of. When the ladies withdrew according to custom, Olney found the tipsy men annoying and joined the women. The men planned some merriment by “rescuing” Olney. Washington unwisely joined the fun by leading the charge into the ladies' parlor, but George Olney wasn't budging, and everything suddenly turned uncomfortable. Deborah held onto her husband as Washington playfully took hold of her wrists. She screamed: "Let go of my hand or I'll pull every hair out of your head! Even if you are a general you are still just a man!" Washington released her and stood back considerably disconcerted.
Caty Greene told the story widely and often, emphasizing how Washington had been deeply embarrassed by Deborah Olney’s common and disrespectful behavior. Apparently Caty was more interested in spiting Mrs. Olney than shielding George Washington from mortification. The discomfiting story eventually got back to Deborah, and her husband appealed to General Washington to set the record straight. He had an aide declare that nothing at all memorable had happened that night. Deborah and Caty exchanged notes that settled nothing except their enduring enmity, but Washington never mentioned this event, which suggests it was a cautionary lesson for him. A reserved man could not play the games of young people, especially with a pretty girl among them, unless he wanted to become something he could not afford to be. Leading the “rescue” of George Olney had been a mistake, one that could have been costly in squandering the aura of authority necessary to lead men in war and government. This happened ten years before he became president.
He would never allow it to happen to him again, but it suggests that when he was younger, when fiddles squeaked and girls giggled and he wasn’t worried about being the George Washington he later felt it necessary to become, he had his moments.