Valentine’s Days were unusually eventful for Theodore Roosevelt and family, as this date marked some of the happiest and darkest periods in their lives. On February 14^th of 1880, the 21-year-old future president publicly announced his engagement to Alice Hathaway Lee. The two previous years of dating sparked a short but intensely happy bond. Teddy and Alice were married the next October and, four years later, welcomed their first child.

On Valentine’s Day of 1884, Teddy was getting used to first-time parenthood. Baby Alice (named after her mother) was born just two days earlier, while he was away and he was eager to return home to spend time with his growing family.^[1] But what should have been a joyous time quickly turned tragic.

The future President received word that his mother, Mittie, was dangerously ill and came rushing home. Soon after he arrived, Mittie passed away from typhoid fever. Unfortunately, Teddy’s shock was not at its end, since at that same time, only a few steps away from Mittie’s deathbed, his wife Alice was also suffering from a life-threatening illness. She passed away that afternoon from Bright’s disease, leaving Teddy suddenly motherless, wifeless, and alone in caring for a newborn baby.^[2] The abrupt death of the two most important women in his life was devastating as Teddy wrote in his famously short and heartbreaking diary entry of February 14, 1884: “The light has gone out of my life.”^[3]

Fast forward to mid February 1906 where the White House was the scene of marital bliss when President Teddy Roosevelt’s daughter Alice prepared to wed her fiancé, Nicholas Longworth. The public eagerly anticipated the national event for months as the D.C.-darling, fondly nicknamed “Princess Alice,” had taken over the spotlight. She frequently attracted attention as a young socialite of the capital city, fueling her celebrity through the independent attitude that set her apart from typical women of her time, and her well-documented antics like smoking on top of the White House^[4] and keeping a pet snake named Emily Spinach.^[5] As her untamable behavior continued through her father’s presidency, Teddy famously proclaimed, “I can either run the country or I can attend to Alice, but I cannot possibly do both.”

Getting married at the White House was a particularly special event since she and Longworth are one of very few couples to boast such an honor. (Even now White House weddings are infrequent. The most recent was in May of 1994, when Hillary Rodham Clinton’s brother, Anthony Rodham married Nicole Boxer.)^[6] For Alice’s ceremony, the East Room was luxuriously decorated and covered in elaborate floral arrangements, leading many spectators to declare that it was the most magnificent wedding the White House had ever seen.^[7] As the husband-to-be of such a well-loved public figure, Longworth inevitably came from a wealthy and highly esteemed background and was considered a suitable match for Alice. When reflecting on the ceremony, one journalist for The Washington Post remarked, “the United States had given to one of its very best sons its very best daughter, its Alice, really the daughter of the President of the greatest country known to contemporary history, but in love and affectionate regard none the less the daughter of all of the American people.”^[8]

Twenty years later, in 1925, Valentine’s Day would again become a date of major change for the Roosevelt family when Alice gave birth to her first daughter, Paulina. The child was living evidence, however, of marital problems that guests at the luxurious wedding ceremony years earlier could not have predicted. Paulina was not the biological child of Nicholas Longworth. Her father was Idaho Senator William Borah, with whom Alice had a long-running an affair.^[9]

From births to deaths, and engagements to marriages, it’s hard to imagine that any other family could match the Roosevelts when it comes to memorable Valentine’s Day experiences. Hope yours is a little less complicated!