Before marrying Clementine, Winston Churchill had proposed to three other women

Churchill's first great love was usually thought to be Pamela Plowden. She rejected his several offers and years of courtship with many letters from him, but she eventually married someone else. Churchill later fell in love with American actress Ethel Barrymore, but she also turned down his marriage proposal. Then Muriel Wilson captured his attention, and despite him taking her on a romantic vacation to Venice, she also declined. Churchill began seeing Clementine Hozier in 1908, and they were married five months later. Churchill proposed to Clementine Hozier in his personal life, they were wed on September 12, 1908, at St. Margaret's, Westminster, and spent their honeymoon in Baveno, Venice, and Vever Castle in Moravia. Despite having five children with Winston, Clementine did not spend much time with them. She put her support behind her spouse instead.

Winston and Clementine, however, were both severely scarred by the terrible death of her daughter Marigold when she was only two years old. A few years later, when Mary, her second daughter, was born, the parents decided to raise her differently. The couple's oldest daughter, Diana, committed suicide in the 1960s by overdosing on drugs. She was the only Churchill child to grow up without having to deal with drinking, divorce, or suicide. Randolph had suicidal thoughts, and Sarah married three times—once secretly and without her parents' consent. Before his passing, Churchill and Clementine were wed for more than 56 years. Due to Winston's busy schedule, the pair spent a lot of time apart even though they kept up frequent contact. Churchill's career depended on the success of his marriage because Clementine's undying love gave him a stable and contented foundation.