Terry married three times and was involved in numerous relationships. In London, during her engagement at the Haymarket Theatre, she and her sister Kate had their portraits painted by the eminent artist George Frederic Watts. His famous portraits of Terry include "Choosing", in which she must select between earthly vanities, symbolised by showy but scentless camellias, and nobler values symbolised by humble-looking but fragrant violets. His other famous portraits of her include "Ophelia" and "Watchman", and, with Kate, "The Sisters". He proposed marriage to Terry in spite of his being three decades her senior. She was impressed with Watts's art and elegant lifestyle, and she wished to please her parents by making an advantageous marriage. She left the stage during the run of Tom Taylor's hit comedy "Our American Cousin" at the Haymarket, in which she played Mary Meredith.