Rodrigo Duterte, November 14

This was, somehow, not the most awkward handshake of the year. When Trump attended the Association for Southeast Asian Nations conference in the Philippines last month, he engaged in the traditional group handshake, and appeared to be overwhelmed by the cross-body action it requires. Per The Telegraph, Trump finally mastered this shake, but he grimaced as he first gripped the hands of the leaders near him, including President Rodrigo Duterte of the Philippines, a man who has defended the killing of journalists.

James Comey, January 22

In January, days after the inauguration, Donald Trump held a ceremony to honor law enforcement officials in the White House’s Blue Room, and noticed in the crowd then-F.B.I. director James Comey. When Trump called Comey to the front of the room, he extended his hand, but while mid-shake, also went in for the hug. It was an awkward handshake that, in retrospect, is entirely ominous; months later, Trump fired Comey, just as the investigation into possible collusion between the Trump campaign and Russia was beginning. Comey, as recounted in his famous Senate hearing, had plenty of reasons to dislike Trump, but the handshake was a surprisingly big one. “Comey was disgusted,” Comey’s friend Benjamin Wittes later wrote in a post on Lawfare, where he is editor-in-chief. “He regarded the episode as a physical attempt to show closeness and warmth in a fashion calculated to compromise him before Democrats who already mistrusted him.”

Emmanuel Macron, July 14

Enough handshake to inspire cringes to last the next three years. During his visit to France in July, the president met with newly elected French president Emmanuel Macron, and shook his hand. And shook his hand, and shook his hand, and shook his hand. This hand-to-hand interaction just did not quit. Then, he hugged the French First Lady, Brigitte Macron, and took hold of her hand and shook it, while still holding tight to her husband. It was the handshake that never ended, and neither did the awkwardness. If you’re really quiet, you can still hear this handshake slicing through the wind as Trump keeps a tight hold on Macron’s fingers, which are likely numb. “My handshake with him, is not innocent,” the famously liberal Macron told the Journal du Dimanche in an interview following a separate infamous handshake he had with Trump at the NATO Summit in Brussels in May. “It’s not the alpha and the omega of politics, but a moment of truth.”