In 2002, Angela Merkel was the head of what was then Germany's main opposition party, the Christian Democratic Union (CDU). Putin was the fresh-faced president of a new and modern Russia. After meeting Putin in the Kremlin, Merkel reportedly joked to her aides that she had passed the "KGB test" of holding his gaze — an allusion to Putin's earlier career in the Soviet security agency.

Putin had built a friendship with Angela Merkel's predecessor, Gerhard Schröder, and the two men remain close to this day. By late 2005, however, it was clear that Merkel was set to dethrone the Social Democrat Schröder. Talking to Merkel in Russia's Berlin embassy, Putin pledged to expand the ties between the two countries. Merkel described the dialogue as "very open."

About a year later, Putin shared his impressions of the woman who had since become Germany's chancellor: "We don't know each other on a very personal level, but I'm impressed by her ability to listen," he told Germany's public broadcaster MDR from Dresden, adding that listening was a rare skill among female politicians.

The German chancellor has a well-known fear of dogs. Still, Putin let his black lab Konni wonder around the Sochi venue when he welcomed Merkel there in January 2007. Was he trying to intimidate her? Merkel seems to think so: "I believe the Russian president knew very well that I wasn't thrilled by the idea of meeting his dog, but he still brought it with him," the chancellor said in 2015.

By 2012, Vladimir Putin had taken on a harsher course towards the press and political dissenters. When asked about media freedom while in Saint Petersburg, Merkel responded with a barely hidden jab at her fellow leader: "If I were to get sulky every time I opened a newspaper, I wouldn't last three days as chancellor," she said.

Relations between Moscow and the West took a steep plunge after the annexation of Crimea in 2014. However, Putin told German media that he still maintained a "business-like relationship" with the German chancellor. "I trust her. She is a very open person. She, like anyone else, is subject to certain limitations, but she is honestly attempting to solve the crises," he told Bild, a German daily.

"I don't mean to insult anybody, but Ms. Merkel's statement is an outburst of a long-accumulated anger over limited sovereignty," Putin told the press in 2017, commenting on an election campaign address that the German leader had given in Munich. Merkel's so-called "beer tent" speech saw her urge Europeans to rely on themselves amidst disputes with US President Donald Trump.

Just a month after Putin's remarks on sovereignty, the two leaders were photographed talking at a G-20 summit in Hamburg. While the topic remains a mystery, both Merkel and Putin used strong gestures. At one point, as Putin wags his finger Merkel looks away from him and rolls her eyes. The moment quickly went viral.

When Merkel arrived in Sochi in 2018, Putin welcomed her with a bouquet of flowers. An offer of peace? An act of gallantry? Sexism? The rationale didn't really matter in the big picture. Appearing alongside Putin, Merkel said dialogue needed to go on. "Even if there are grave differences of opinion on some issues, we have to talk to each other, because otherwise you just sink into silence."

Angela Merkel met with the Russian President in the Kremlin in January 2020. Later, relations again deteriorated over the Russian involvement in Ukraine, but also over its treatment of dissidents. Most notably of dissident Alexei Navalny who was arrested upon his return to Russia from medical treatment in Germany.