The first woman to become Theodore Roosevelt's wife was Alice Hathaway Lee. She was only 17 years old when they met on October 18, 1878 at the home of her neighbors, the Saltonstalls, whose son Richard was classmates with Teddy at Harvard University. Teddy felt that he had fallen in love with Alice from first meeting, and by Thanksgiving – a few weeks after they met – had already decided he would marry her. In June 1879, Teddy proposed to Alice, but she took more than eight months to give him an answer. During this time, Theodore enlisted the help of his mother and sisters to help him court her, finally receiving her 'yes' on February 13, 1880. They announced their engagement the next day – Valentine's Day.
The couple married on October 27, 1880 (Teddy's 22nd birthday) at the Unitarian Church in Brookline, Massachusetts. As of the date of their marriage, Alice was only 19 years old. In attendance at their wedding and reception at the home of Alice's parents was a woman named Edith Carow, who would later become Teddy's second wife. Following the wedding, the couple had to delay their honeymoon, due to Theodore being accepted into Columbia Law School. Instead, they spent two weeks at the Oyster Bay Roosevelt family home, and subsequently moved in with Teddy's now-widowed mother, Martha.
In 1883, the happy couple announced the impending birth of their first child. After great anticipation, the joyful pair welcome a baby girl – Alice – at 8:30 p.m. on February 12, 1884. At the time of her birth, Theodore was out of town in Albany, for business on the Assembly Floor. Convinced the child would be born on Valentine's Day (his fourth engagement anniversary with his wife), he had not made arrangements to be there until the following day. The morning of February 13, he received a telegram about the birth and began making arrangements to leave. Sadly, he later received a telegram that his wife was ill and didn't arrive at her bedside until she was semi-comatose. While at his wife's deathbed, he received the devastating news that his mother – below him, in the same house – was also dying from what was later diagnosed as typhoid fever. His mother died early in the morning of February 14; his wife died several hours later, on what would have been their fourth engagement anniversary, at the age of 22. He wrote in his diary entry for that day, "The light has gone out of my life", then almost never spoke of her again, except for a privately-published written tribute to her. When their daughter (Alice) asked him about her mother, he was still so distraught he told her to ask his sister ("Bamie") for information. He even refused to mention his beloved in his autobiography.
Teddy married his second wife, Edith Kermit Carow Roosevelt, on December 2, 1886 in London, England. During the ceremony at St. George's Church of Hanover Square, the fog was so thick it filled the church. After a 15-week honeymoon all over Europe, the couple returned to the U.S. and lived at a house on Sagamore Hill, in Oyster Bay. As the First Lady (from 1901-09), she fiercely guarded her family's privacy and acted as a gentle, smiling hostess for all social events held at the White House. She and Teddy were the parents of five children: Theodore III, Kermit, Ethel Carow, Archibald Bulloch, and Quentin. Following Teddy's death in 1919, she traveled, helped provide clothing for the poor, and even briefly campaigned for Herbert Hoover during his re-election bid in the 1932 presidential election. Interestingly, her support of Hoover's re-election campaign pitted her against her own cousin- and nephew-in-law, Franklin D. Roosevelt.