It is sometimes hard to discern what Jefferson's humor was like, but there are references to Jefferson's sense of humor from family accounts, from his letters, and from contemporary descriptions.
An anecdote related by Ellen Wayles Harrison, daughter of Thomas Jefferson Randolph: "When Mr. Jefferson visited the mother (Martha J. Randolph) on the birth of her twelfth child, he in playful reproach said, 'My dear! We shall have to send you back to the convent!'"
As a young man, Jefferson once proposed the date of February 30th for a race between his slow pony and Dabney Carr's fast horse.
In the Entrance Hall at Monticello, Jefferson placed a likeness of himself and his political opponent Alexander Hamilton opposite one another. One of Jefferson's grandchildren said, "the eye settled with a deeper interest on busts of Jefferson and Hamilton, by Ceracchi, placed on massive pedestals on each side of the main entrance--'opposed in death as in life,' as the surviving original sometimes remarked, with a pensive smile, as he observed the notice they attracted.
John Quincy Adams said, "Mr. Jefferson tells large stories...you never can be an hour in this man's company without something of the marvellous, like these stories." Adams recalled the story of Jefferson, who sailed on the Ceres, a voyage of nineteen days, studied Spanish by reading Don Quixote with the help of a grammar. Jefferson later remarked that it was a very easy language since he had learned it in a voyage of nineteen days.
Frances Few, in 1808 described Jefferson, "I dined with the President--he is a tall thin man very dignified in his appearance but very agreeable in his manners--his face expresses great good humour--there is scarce a wrinkle on his brow--he seems very happy."
Jefferson described by John Bernard, 1801, "his information was equally polite and profound and his conversational powers capable of discussing moral questions of deepest seriousness, or the lighter themes of humor and fancy."
Jefferson to Abigail Adams, "I have also procured for you three plateauz de dessert with a silvered balustrade round them, and four figures of Biscuit...with respect to the figures I could only find three of those you named, matched in size. These were Minerva, Diana, and Apollo. I was obliged to add a fourth, unguided by your choice. They offered me a fine Venus; but I thought it out of taste to have two at table at the same time...At length a fine Mars was offered..."
In 1823, Alexander Hugh Holmes Stuart wrote, "I have never met any one who presided at his own table, with the same playful grace and urbanity, blended with perfect dignity..."
↑ Ellen Wayles Harrison and Martha Jefferson Trist Burke, Monticello "Child Life" - Memories of What We Heard from our Parents, manuscript, Jefferson Library, Thomas Jefferson Foundation.