The Boston portraitist Sarah Goodridge painted this intimate self-portrait for the statesman Daniel Webster in 1828, the year of his first term as U.S. Senator. Their association is documented in forty-four letters that Webster wrote to Goodridge between 1827 and 1851. Webster sat for her at least twelve times over two decades, and she visited him in Washington, D.C.—the only time she is known to have left Boston. This provocative twist on the traditional lover's eye miniatures so popular in London demonstrates the artist's command of nuances of light and shadow and glowing tones captured through the use of transparent washes of watercolor on ivory.