This was a "Quora" question, and yes it "almost" happened, but Hitler did a "No-show". I thought it was an interesting question.
In late summer 1932, Winston Churchill and Adolf Hitler nearly dined together at a Munich hotel, until one blunt question caused Hitler to stand Churchill up.
At the time, Churchill was in his "wilderness years"—out of power and holding no official government office. He was traveling through Germany researching a biography of his ancestor, the Duke of Marlborough, and settled into Munich's Hotel Regina.
Also staying at the Hotel Regina was Ernst "Putzi" Hanfstaengl, an eccentric, Harvard-educated German-American who served as Hitler's foreign press chief. Hanfstaengl recognized Churchill and introduced himself. Eager to bridge a connection between the rising Nazi leader and the famous British statesman, Hanfstaengl mentioned that Hitler was coming to the hotel that evening and suggested they meet for dinner. Churchill agreed.
Later that day, while having drinks with Hanfstaengl, Churchill probed his new acquaintance about the Nazi party's aggressive policies. Churchill remarked that he could understand being angry with people who have done wrong, but asked, "Why is your chief so violent about the Jews? ... What is the sense of being against a man simply because of his birth? How can any man help how he is born?"
Hanfstaengl, recognizing the danger of bringing such a critical stance to his boss, rushed off to relay the conversation to Hitler, hoping the Nazi leader would still see political value in the meeting. Instead, Hitler refused to join him. He reportedly dismissed the invitation entirely, asking, "What part does Churchill play? He is in opposition and nobody attends to him."
Hitler never appeared, standing Churchill up. The two men never crossed paths. Churchill later wrote in his memoirs that this near-miss in Munich was the only time he ever came close to speaking with the man he would eventually lead Britain against in the Second World War.


