There have been so many new lows in the relationship between President Obama and his Russian counterpart, Vladimir Putin, that it’s easy to forget how confident Obama was in forging a new partnership with the Kremlin after his election in 2008.

Before the showdown with Putin over Ukraine and sparring over Edward Snowden's asylum, Obama was trumpeting a reset with Russia and openly mocking critics of his approach as being stuck in the Cold War.

But now even the president would likely concede he was overconfident in his abilities to influence Putin’s thinking or deter the former KGB officer from doing what he wanted to enhance Russia’s prestige.

The Obama-Putin tango has always been one thing: awkward.

What once was an uncomfortable courtship, however, has given way to the reality that Obama and Putin are done with each other. Here’s how it happened:

March 2009: Secretary of State Hillary Clinton presents Russian Foreign Minister Sergey Lavrov with a “reset button.” "I would like to present you with a little gift that represents what President Obama and Vice President [Joe] Biden and I have been saying and that is: 'We want to reset our relationship and so we will do it together,'" she says. In a bit of foreshadowing, the Obama administration gets the Russian translation on the button wrong.

April 2009: Obama promises a “fresh start” with Russia, striking a deal with Russian President Dmitry Medvedev to begin negotiations about how to shrink the nations’ nuclear arsenals. At the time, Putin was serving as Russia’s prime minister, but was seen as the man calling the shots.

April 2010: The U.S. and Russia sign a New START agreement, reducing the nuclear stockpiles of both nations by 1,500 warheads.

March 2012: A hot mic picks up Obama telling Medvedev, “After my election, I have more flexibility." Medvedev responds by saying he’ll pass along Obama’s message to Putin, who will soon reclaim his post as Russian president. Critics pounce on the remark as proof that Obama is making shortsighted concessions to Putin.

December 2012: With congressional passage of the Magnitsky Act, Russian officials tied to the death of accountant Sergei Magnitsky — he died in Russian police custody, prompting humanitarian complaints — are banned from entering the U.S. and have their American assets frozen. Putin vows a proportional response.

December 2012: Not long after the Magnitsky spat, Putin pushes through a law that prohibits Americans from adopting Russian children. The Russians name the bill after a 2-year-old adopted Russian child who died after being left in a hot car by his adopted American father.

June 2013: The U.S. pressures Russia to condemn the use of chemical weapons by strongman Bashar Assad’s regime in Syria’s civil war. Instead, the Russians cast doubt on western claims and blame the Syrian rebels for the violence in the war-torn nation.

August 2013: Defying U.S. demands, the Russian government grants asylum to Snowden, the NSA leaker, ratcheting up the animosity between Washington and Moscow. Putin rebuffs all requests to send the former government contractor to the U.S., stoking an embarrassing episode for the Obama administration.

August 2013: In response to the Snowden asylum, the White House abruptly cancels one-on-one talks scheduled for the two leaders in St. Petersburg.

December 2013: With protests in Kiev spiraling out of control, Putin announces that the Kremlin will purchase $15 billion in Ukrainian government bonds. By propping up the regime of Ukrainian President Viktor Yanukovych, Putin undermines U.S. calls for the Ukrainian leader to listen to the demands of his people. At Putin's behest, Yanukovych had already rejected calls for the country to join the European Union, initiating the violent protests.

February 2014: After fleeing Ukraine, Yanukovych reappears in Russia and Putin begins military exercises on Ukraine’s border.

March 2014: Obama begins issuing sanctions against Russian separatists in Ukraine following the seizure of military posts in Crimea by Putin sympathizers.

March 2014: With the Sochi Olympics completed, Putin officially signs off on the Russian annexation of Crimea, igniting dueling sanctions in Washington and Moscow.

March 2014: The U.S. and Western allies vote to force Russia out of the Group of Eight nations, a rebuke meant to punish Putin for the annexation of Crimea. Putin, however, steps up Russian incursions into Eastern Ukraine.

May 2014: Medvedev, now Russia’s prime minister, accuses the Obama administration of trying to start a “second Cold War.”

June 2014: Obama travels to Europe for a major presidential trip, framing the Ukrainian crisis as the centerpiece of his visit. “The days of empire and spheres of influence are over. Bigger nations must not be allowed to bully the small, or impose their will at the barrel of a gun or with masked men taking over buildings. And the stroke of a pen can never legitimize the theft of a neighbor’s land,” he says in Poland.

June 2014: In a possible breakthrough, Putin tells Obama in a telephone conversation that he is committed to stopping the violence in Southeast Ukraine.

June 2014: The next day a ceasefire in Ukraine is violated when Russian separatists shoot down a Ukrainian military helicopter.

July 2014: Putin issues his strongest condemnation of U.S. sanctions to date. "Sanctions have a boomerang effect and without any doubt they will push U.S.-Russian relations into a dead end, and cause very serious damage,” he says.

July 2014: A Malaysia Airlines passenger jet is shot down in Ukraine. After initially refusing to assign responsibility for the attack, the White House says Putin's regime is “culpable” for the deaths of nearly 300 passengers and crewmembers.

July 2014: Wanting to get in on the Putin bashing, Biden reveals in an interview that he once told the Russian president, “I don’t think you have a soul.”

July 2014: The Obama administration concludes that the Russian government violated a major arms control treaty by testing long-range missiles.

July 2014: For the first time, the U.S. and European nations unite behind major sanctions against the Russian energy, arms and finance industries. The Western powers say the downing of the passenger jet forced their hand.