Prior to his meetings with Soviet leader Nikita Khrushchev, President Kennedy's advisors endeavored to prepare him for what was expected to be a demanding encounter. The consensus among his advisors was that Khrushchev would likely attempt to intimidate Kennedy. The inaugural meeting took place at the US Ambassador to Austria's residence in Vienna on June 3, 1961, during the early afternoon. The discussion between Khrushchev and Kennedy primarily revolved around their respective economic systems and was marked by a lively debate. The atmosphere improved over lunch, but tensions resurfaced when the two leaders took a garden stroll later. During the walk, Khrushchev persistently criticized both Kennedy and the US economic system.

Later in the day, Dave Powers noted how composed the President appeared during Khrushchev's verbal attacks. Kennedy responded, "What did you expect me to do... take off my shoe and hit him over the head with it?"

The afternoon meetings didn't fare any better, as Khrushchev continued his unrelenting assault on Kennedy and American policies. That evening, a state dinner was held at the Schönbrunn Palace. Afterward, Khrushchev confided in his aides, describing Kennedy as "very young, not strong enough; too smart and too weak." The following day, the conversation shifted to focus on Berlin and Germany. Khrushchev asserted that he would sign a peace agreement with Germany, regardless of US approval or consideration for US rights in West Berlin. Kennedy clarified that while signing a peace agreement was not an issue, infringing on Western rights could potentially lead to war.

Upon the conclusion of the formal meetings, Kennedy insisted on a brief private meeting with Khrushchev. During this encounter, Khrushchev declared, "Force will be met by force. If the US wants war, that's its problem. It is up to the US to decide whether there will be war or peace. The decision to sign a peace treaty is firm and irrevocable, and the Soviet Union will sign it in December if the US refuses an interim agreement." Kennedy retorted, "Then, Mr. Chairman, there will be a war. It will be a cold winter." The meeting left Kennedy profoundly shaken. He confided in James Reston afterward, describing the encounter as the "worst thing in my life." Kennedy had been confident that he could charm Khrushchev and reach a mutual understanding, but now he perceived war as a genuine possibility. This confrontation with Khrushchev prompted Kennedy to reevaluate US policy on a global scale.