She attracted many admirers including Oliver Wendell Holmes Jr., Robert Todd Lincoln; and stage actor and presidential assassin John Wilkes Booth, to whom she was secretly engaged.

[1] Her manner toward men was a "subtle brew of flattery, teasing and cajoling; of rapt attention laced with a hints of indifference and occasionally a touch of cruelty".

Her father had entertained the hope that Lucy would marry Robert; and although Senator Hale's wishes did not come to fruition, the couple would remain good friends for many years.

[1] When the Civil War broke out in April 1861, she, her parents, and her sister Elizabeth went to live at the National Hotel in Washington, D.C., and she began working for the Sanitation Committee.

To see you has indeed afforded me a melancholy pleasure, if you can conceive of such, and should we never meet nor I see you again believe me, I shall always associate you in my memory, with her, who was very beautiful, and whose face, like your own I trust, was a faithful index of gentleness and amiability.

There was no reason to suspect that Hale knew anything of the plot to kill the president, nor was she aware of the deep antipathy her fiancé felt towards Lincoln.

At 8 p.m. he allegedly looked at his watch, stood up, and after taking her hand in his, recited some lines from William Shakespeare's Hamlet: "Nymph, in thy orisons [prayers], be all my sins remembered".

[6] She wrote a letter to his brother, Edwin, expressing her shock and sorrow, while her father published notices in the press denying there had ever been an "intimate connection" between his daughter and Booth.

There were rumors that she had gone, heavily veiled, aboard the USS Montauk in the Washington Navy Yard to view the body of Booth which lay in one of the cabins, and upon seeing it, threw herself on him, sobbing.

[1] France, Italy, and Switzerland, were among the countries she visited; in Paris she attended the theatre with her former beaux Oliver Wendell Holmes Jr., John Hay, and Frederick Anderson.

In 1870, she returned to America to care for her sick father, and renewed a correspondence with her first admirer, the successful corporation lawyer William E. Chandler, whose wife, Ann Gilmore had died.