For reasons both sentimental and political, the last few years have witnessed a renewed torrent of interest in the presidency of John F. Kennedy. A range of authors—from horror writer Stephen King to TV personalities Chris Matthews and Bill O’Reilly to political scientist Larry Sabato—have ventured their own distinct interpretations on the brief but eventful Kennedy years. The imminent fifty-year anniversary of Kennedy’s assassination in Dallas promises to spark renewed intense debate.

Most of these discussions will hinge on well-known events: the Cuban Missile Crisis, the Bay of Pigs, and Kennedy’s response to the March on Washington. Many will pose intriguing but fundamentally unanswerable hypothetical questions, such as where Kennedy’s Vietnam policy was heading whether he might have achieved detente with the Soviet Union. Others will wonder how Kennedy might have responded to contemporary events. The most fruitful questions, however, will be those that ponder the enduring lessons of Kennedy’s tenure, and how they might inform our own efforts to deal with a complex world. In the wake of Iranian president Hassan Rouhani’s visit to the United Nations, one is especially provocative: JFK’s willingness to meet with often-hostile foreign leaders.

Kennedy’s record of presidential diplomacy forms a powerful contrast to the prevailing assumptions of the present day. His first year in office witnessed numerous meetings with foreign leaders—many of them neither aligned with the United States, nor well regarded by the American electorate. He received Ghana’s Kwame Nkrumah, a frequent critic of U.S. policy in Africa. India’s Jawaharlal Nehru, often derided for his decision to remain nonaligned in the Cold War, paid Kennedy an autumnal visit. Indonesia’s Sukarno, whom the CIA had tried to undermine a few short years earlier, visited the White House twice. Most fatefully of all, Kennedy met with Soviet General Secretary Nikita Khrushchev for two tense days in Vienna.

The Vienna summit is Kennedy’s best-known meeting with a foreign leader and enjoys a dubious reputation. Fresh from the Bay of Pigs fiasco, yet hoping to connect with his Soviet counterpart, Kennedy endured two contentious days of argument with the feisty Khrushchev, who had clearly arrived in a combative mood. “Vienna” has become a popular byword for disastrous summits—a cousin of sorts to “Munich”—yet there is cause to question this verdict.

Khrushchev, we now know, faced considerable pressure within the communist bloc to resolve the problem of Berlin—the main topic of discussion in Vienna. This propelled him toward positions likely to provoke Kennedy, and he dismissed sage counsel from his advisor Anastas Mikoyan not to underestimate the new president. Khrushchev proceeded to do so, but he needed little help from Kennedy in that regard, as he was dangerously prone to mood swings and wishful thinking. Kennedy, hoping to forge an early bond with the Soviet leader, was shocked by Khrushchev’s bellicosity, but the transcript of the meeting stands at odds with the popular image. Although he vented his frustration after the fact—as he often did in the face of disappointment—Kennedy seems to have given as well as he received. One could make the case that he should not have met with Khrushchev after the Bay of Pigs, but that argument seems a surrogate for a more compelling one: that Kennedy should have vetoed the Cuban operation.

In spite of the acrimony, Kennedy was better off for having met Khrushchev, even if he did not realize it immediately. The two leaders did arrive at an important compromise over the Cold War battleground of Laos. Over the ensuing months, Kennedy adopted a prudent middle course on the Berlin question: increasing military preparedness while avoiding more the provocative steps urged by some of his advisors. Most powerfully of all, his two days with Khrushchev doubtless influenced his careful leadership during the autumn 1962 Cuban Missile Crisis, when he showed a repeated (albeit imperfect) inclination to put himself in his adversary’s shoes. His tribulations in Vienna were inseparable from his later successes, both during the crisis, and during the months that followed it, which witnessed a remarkable easing of U.S.-Soviet tensions.

His other head-of-state meetings were generally successful. Kennedy was energetic and attentive and his guests almost invariably found him informed and charming. The interpersonal bonds he forged with them served to limit (though not preclude) conflict. His November 1963 death would be widely mourned, from Moscow to New Delhi to Jakarta.

If Kennedy could advise his successor today, he would urge outreach toward Iran. The gulf between Washington and Tehran remains broad on issues such as Syria and Iran’s nuclear program, yet recent events reveal a real window of possibility. Despite the looming shadow of Syria, the prospect of a Vienna-like confrontation in a hypothetical Obama-Rouhani meeting is unlikely. The chance for an encounter at the UN has passed, but both governments would be well advised not to let another such opportunity slip by.

Inevitably the prospect of an Iranian-American dialogue will raise cries that a meeting—in advance of any concessions from Tehran—represents some kind of unilateral concession to the Iranians. That is, as JFK might put it, a “dangerous, defeatist belief”—and one founded on a striking misreading of history. It overrates the political symbolism of a meeting with the U.S. president (a complicated prospect for an Iranian leader) and underrates the importance of the interpersonal ties and unexpected breakthroughs that can flow from such a summit. Legislators or pundits prepared to assail Obama for the slightest slackening of pressure on Iran might well consider how Ronald Reagan benefited from Margaret Thatcher’s early meeting with Mikhail Gorbachev, or his own November 1985 summit with the Soviet leader.

Approaching the solemnity of this coming November 22, we can ask all the usual provocative questions about Kennedy’s world. Undoubtedly we will. But there are benefits to looking further afield, and asking what lessons his presidency offers for the present day. As he himself put it: “Let us never negotiate out of fear, but let us never fear to negotiate.”

Robert Rakove is a lecturer in the Program in International Relations at Stanford University.