Stalin and Hitler never met, nor did they ever actually talk to each other. The same goes for Churchill and FDR who never talked to Hitler either. The only allied leader that I can think of who actually met and talked with Hitler and then later fought him in World War Two was Canada's prime minister, William Lyon Mackenzie King. Also Chamberlain and the French prime minister Édouard Daladier. Hitler did however write Stalin a letter and he had Ribbentrop give it to Stalin personally. The letter states that both sides should unite against the allies and that the Soviets should support the German claims in Poland. Its been speculated that Stalin and Hitler may have talked one the phone, but no evidence for such a meeting actually exists. The closest Hitler got was his meeting with Soviet foreign minister Molotov in Berlin in 1940.
Also for anyone curious (and because it feels weird to have such a short post) here is a list of countries who's prime ministers or presidents met with Hitler at least once:
Britain (Neville Chamberlain)
Canada (PM William Lyon Mackenzie King)
France( PM Édouard Daladier)
Italy (The King- Vittore Emmanuel III and Mussolini)
Czechoslovakia (President- Emil Hácha)
Hungary (The Regent- Milkos Horthy and the PMs Béla Imrédy and Paul Teleki)
Romania (Prime ministers Ion Antonescu and Ion Gigurtu King Carol II )
Bulgaria (king Boris III)
Slovakia (Prime Minister Jozef Tiso)
Croatia (Prime minister Ante Pavelic
Vichy France (Prime Minister Pierre Laval and President Phillipe Petain)
Spain (Fransico Franco)
Yugoslavia (PM-Dragisa Cvetkovic)
Belgium (King Leopold III)
Finland (Mannerheim)
Churchill agreed to meet with Hitler before the war when they were both in Munich:
However, Churchill had a couple questions for Hitler than probably changed Hitler's mind
This is a really interesting question, and I actually just finished reading a book about this possibility. It's called Hitler's Peace, by Philip Kerr. Here's part of the summary from Google Books:
Autumn 1943. Since Stalingrad, Hitler has known that Germany cannot win the war. The upcoming Allied conference in Teheran will set the ground rules for their second front-and for the peace to come. Realizing that the unconditional surrender FDR has demanded will leave Germany in ruins, Hitler has put out peace feelers. (Unbeknownst to him, so has Himmler, who is ready to stage a coup in order to reach an accord.) FDR and Stalin are willing to negotiate. Only Churchill refuses to listen.
It's a really fascinating historical fiction story, effectively weaving hypothetical happenings within actual events. If you're wondering what such an event might have looked like, I think this book would be a good read.
Mods: I apologize if this is against the rules - I couldn't find anything prohibiting it.
Sorry for the followup question, but how did they actually communicated during war time? Telegraph? Phone? Written letters?
The reason I'm curious is that if communication was mantained via wires, did both sides had any agreements about not destroying/razing certain wirings or poles for the sake of mantaining contact?
I'm not sure how to word this but was there communication between the countries? did representatives from each country talk?
Following this, was there any diplomatic contact by the allies with Germany during the war?
There is a change Stalin and Hitler met before they rose to power.
According to this "popular" article: http://www.bbc.com/news/magazine-21859771
FDR = F.D. Roosevelt???