Da Ponte's son, a New York University professor, befriended the teenaged Dan Sickles and helped secure him a scholarship to the University. Young Sickles also moved into the Da Ponte home; he left after about a year when his mentor suddenly died but maintained close ties with the family, possibly to continue the study of French and Italian. Though Sickles had known Teresa since her infancy, he made her acquaintance again in 1851, this time as an Assemblyman (and part of the Tammany Hall Democratic machine). He was thirty-three years old, she was fifteen.
Sickles, a notorious womanizer, was quite taken with Teresa and soon proposed marriage. Despite his prominence and long connection to the family, the Bagiolis refused to consent to the marriage. Undeterred, the couple wed on September 17, 1852, in a civil ceremony. Teresa's family then relented and the couple married again, this time with John Hughes, Catholic Archbishop of New York City, presiding. Some seven months later, in 1853, their only child, Laura Buchanan Sickles, was born.
Following the election, the Sickles moved to Washington, D.C., where they became quite involved in political society. Congressman Sickles was very influential and Mrs. Sickles was beautiful and charming. The Sickles hosted formal dinners every Thursday, and Teresa was "at home" (available to callers) to other society ladies every Tuesday morning. With her husband, she attended most of the major social events of the day. Teresa Sickles, Harper's reported, quickly had become a fixture in Washington society. She was especially celebrated as a hostess who was capable of charming the most sophisticated guest while simultaneously making the most socially inexperienced feel at home. It was also said that Teresa and Dan became good friends of Mary Todd Lincoln and Republican Abraham Lincoln despite Dan being from a different party. Teresa attended seances held by Mary Todd Lincoln, who was noted for her interest in spirituality. It was reported that Mary Todd Lincoln gifted a necklace engraved "From Mary Lincoln to Laura Sickles" to Teresa's daughter in 1853, early in their friendship.
As in New York, Sickles continued to maintain love affairs in Washington and, in the meantime, seriously neglected his marriage. It did not take Teresa long, however, to strike up a romance of her own with Phillip Barton Key, a U.S. District Attorney and son of Francis Scott Key, the author of "The Star-Spangled Banner". Philip's uncle was Roger B. Taney, Chief Justice of the United States, and, in 1857, Philip became one of the pillars of the Washington bar. Key followed Teresa everywhere, to her social gatherings as well as to her home.
Dan Sickles eventually received a poison pen letter informing him of his wife's infidelity and investigated further. He discovered the allegations were true, and that Teresa and Key even had a house for their assignations--located within walking distance in a poor, mixed-race part of town.
Sick with rage at his discovery, Sickles confronted his wife. Though she initially denied everything, Teresa eventually relented and wrote out a confession. In the extraordinarily candid document, Teresa described her numerous rendezvous with Key at a vacant home on 15th Street, a house that Key rented. A few days later, on Sunday, February 27, 1859, Sickles saw Key outside his house, located on the west side of today's Lafayette Square, signaling Teresa with a handkerchief. Key continued walking, and Sickles sent an acquaintance outside to delay Key. Sickles then armed himself with several pistols, burst from his house, and intercepted Key at the corner of Madison Place N.W. and Pennsylvania Avenue, across the street from the White House. There, Sickles shot the unarmed Key twice, with one shot directed at Key's groin. Key died about an hour later at a nearby house.
Daniel Sickles was later acquitted of the murder in the first use of the insanity defense in the U.S.
Teresa took ill and died of tuberculosis in 1867 at about the age of thirty-one.