London, Nov 11: Winston Churchill first fell in love in Hyderabad in 1896 but was spurned for the son of a Viceroy of India. He suffered heartbreak when his hopes of marrying the love of his life were dashed by his lack of money.
The man who went on to become Britain’s wartime Prime Minister proposed to Pamela Plowden, a renowned society beauty, when he was in his early twenties, and it is thought that they were informally engaged. But just two years later she married Victor, Earl of Lytton. A few months his senior, Plowden was the daughter of Sir Trevor Chichele-Plowden, at that time the British Resident in Hyderabad.
A letter released by Pamela’s descendants shows Churchill was acutely aware that his financial situation was a bar to marriage. Writing from Calcutta in March 1899, he began with "My dear Miss Pamela" and told her: "I have lived all my life seeing the most beautiful women London produces... Never have I seen one for whom I would forego the business of life. Then I met you... Were I a dreamer of dreams, I would say... Marry me and I will conquer the world and lay it at your feet."
For marriage two conditions are necessary — money and the consent of both parties. One certainly, both probably are absent. And this is all such an old story...
The letter is among a set of 40 expected to fetch a six-figure sum when they are auctioned by Christie’s next month. They span 63 years that begin with Churchill wearing his heart on his sleeve in florid love letters, then mature into an affectionate correspondence between friends before, during and after the war.



It was love at first sight and he wrote to his mother: "She is the most beautiful girl I have ever seen." His mother, Lady Randolph Churchill, wrote to him before his return from South Africa: "Pamela is devoted to you and if your love has grown as hers I have no doubt it is only a question of time for you to marry."



In the March 1899 letter, which has a Christie’s guide price of £18,000-£25,000, Churchill contemplates a future without Pamela: "I look to the consolations of life. I enjoy health, brains, youth and the future... God has taken pleasure in inventing an imperfect world. What a God!"



By 1902 Churchill was graciously congratulating Victor, second Earl of Lytton, on his engagement to Pamela, wishing them "all the happiness & good fortune which wit & beauty deserve when they combine to share the inheritance of the future," and trusting he would "always be counted among your most devoted friends."



Six years later, Churchill sends a letter marked "Secret till Saturday," announcing: "I am going to marry Clementine... you must always be our best friend."



Mark James, a specialist in Christie’s books department, told The Observer: "It’s fascinating to see the more intimate side of him. The early letters are terribly passionate, writing at full throttle."



The official collection of Churchill’s papers is held at Churchill College, Cambridge, which does not have funds to bid for the letters.