Jefferson's Failed Teen Romance

Activity: Cut A Silhouette

by Brandon Marie Miller

In 1762, 19-year-old Jefferson fell smitten with Rebecca Burwell, age 16. But the young law student's great shyness prevented him from even speaking to the girl for over a year. Instead, he pined for her and begged his friends for information. When his friend John Page attended a wedding, Jefferson wrote: "Was she there? because, if she was, I ought to have been at the Devil for not being there too."

Courtesy Colonial Williamsburg Foundation

Jefferson worked up his nerve and asked Rebecca for a cut silhouette of herself he could carry in the
back of his pocket watch. But one night his roof leaked, ruining the picture. How could he ask Rebecca for another "after my suffering the other to get spoiled," he wrote Page. Even without the silhouette, "there is so lively an image of her imprinted in my mind that I shall think of her too often, I fear, for my peace of mind."

In October 1763 Jefferson attended a dance with Rebecca at the Apollo Room in Williamsburg's Raleigh Tavern. But the evening dashed poor Thomas's hopes. The next day he wrote Page in anguish: "I was prepared to say a great deal. I had dressed up in my own mind such thoughts...in as moving language as I knew how, and expected to have performed in a tolerably creditable manner. But Good God! When I had an opportunity of venting them, a few broken sentences, uttered in great disorder and interrupted with pauses of uncommon length were the too visible marks of my strange confusion!"

John Page encouraged his friend to try again, but Jefferson feared rejection which would "be ten times more wretched," than if he did nothing at all. Rebecca dropped her tongue-tied, shy suitor. Jefferson threw himself into the study of law and pushed aside thoughts of marriage for many years.

Now, try your own hand at cutting a silhouette while sparing a thought to poor Jefferson and his failed romance!