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The 20 Most Awkward Political Interactions of Recent Memory, Ranked

Inspired by (obviously) Obama and Raúl Castro

During his trip to Cuba this week, President Barack Obama had an incandescently awkward interaction with President Raúl Castro. It can be best summed up as “I’m a Little Teapot” meets “Gumby in the Microwave.”

Since sharing uncomfortable moments with other politicians is laid out as one of the chief duties of the president of the United States in the Constitution, this was not the first time that Obama has made us cringe when attempting a hug or handshake. The president is not alone, either. Being a politician mainly involves realizing, over and over again, that you aren’t much better at socializing with people you’d rather not deal with than the rest of us.

Let us rank some of the most egregious examples of politicians pretending to like each other or accidentally revealing that all they want to do is go home and take online introvert quizzes.

20. Treasury Secretary Tim Geithner and China's Vice Premier Wang Qishan


Just breathe, Hillary told herself. One day, you will rule them all.

19. Barack Obama and Charlie Crist

Chip Somodevilla/Getty

This looks like a pretty benign hug, until you look into the former Republican governor of Florida’s eyes and see that the hope has evaporated — and that he sort of looks like Gob Bluth. Three years earlier, Crist had also given Obama a hug — an embrace he later called the “Hug That Killed My Republican Career.” In 2014, Crist was running for governor again, this time as a Democrat. He told voters, per the Washington Post, “I can’t help it; I have to hug. Can you even imagine not hugging?”

18. Obama and Raúl Castro

Mandel Ngan/Getty

Obama and Castro have a rich history of awkward handshakes. This one, which took place in Panama City, Panama, last year, featured Castro slowly trying to reel in the recalcitrant Obama, who tested how far away he could possibly get from a person while still technically shaking hands with him.

17. John Boehner and Nancy Pelosi

Brendan Smialowski/Getty

Running the House is exactly like dealing with your relatives at Thanksgiving — except doing that every day for eternity.

16. Obama and Secretary of Defense Chuck Hagel

Chip Somodevilla/Getty

When your parents say they aren’t disappointed in your bad math grades, but you know the truth.

15. Obama and Israeli Prime Minister Benjamin Netanyahu

Alex Wong/Getty

When you run out of things to talk about five minutes into a Tinder date.

14. Howard Dean and John Kerry

Mark Wilson/Getty

The former Democratic front-runner briefly thinks about what would happen if he decided to keep trying to win the 2004 presidential election by becoming John Kerry, Face/Off–style.

13. Obama and Paul Ryan

Chip Somodevilla/Getty

One of the most dependable genres of awkward political interactions is when politicians cover up the fact that they are talking with someone they despise by overacting so much that even a former Disney Channel star forced to direct their local community theater troupe 10 years later would tell them that they needed to tone it down a bit.

You aren’t fooling anyone, Mr. President. Also, what is going on with this handshake? You look like you have fallen off the side of a cliff and are begging Paul Ryan to pull you up. Which he could! He's very strong!

12. Obama and Mitt Romney

Mark Wilson/Getty

Obama makes the same exact face every single time he pulls a “HAHAHA THIS IS THE MOST FUN I HAVE EVER HAD.” To date, he has never fooled anyone.

11. Hillary Clinton and Russian President Vladimir Putin

Mikhail Metzel/Getty

The face must be in some “How to Look Like a President” self-help book, because Clinton makes the same exact face as Obama. Still doesn’t work. At all.

10. Obama and Hillary Clinton

Emmanuel Dunand/Getty

Nope, doesn’t work when they try it on each other, either.

9. Japanese Prime Minister Shinzo Abe and Chinese President Xi Jinping

After a long run of successfully ignoring each other, the two leaders agreed to meet at a summit — without relinquishing their vow to ignore each other.

8. Obama and Putin

Chip Somodevilla/Getty

Remember, rosé is the perfect way to de-escalate any awkward staring contests with archnemeses.

7. John Kerry and French President François Hollande

The Secretary of State’s hug-handshake attempt to greet the French president in January 2015 is actually an adaptation of the dance between Mr. Darcy and Elizabeth Bennet in the BBC Pride and Prejudice miniseries, only Hollande did not just emerge from a pond. Probably.

6. Angela Merkel and Hollande

Thierry Chesnot/Getty

Hmm, maybe that hug fail wasn’t John Kerry’s fault.

5. Jim Webb and Bernie Sanders

Joe Raedle/Getty

What happens when a man who can’t stop thinking about the war meets a man who can’t stop thinking about income inequality after they both shoved a bunch of Werther’s Originals in their mouths?

4. Obama and Taoiseach (Irish Prime Minister) Enda Kenny

The “let’s shake ha … oh, no, you thought I was trying to shake hands? No, just looking at my hand here … time for me to get a manicure, definitely. Just making a fist while I keep all my emotions inside, nothing to watch here … look at these walls. So many nice paintings, hmm?”

3. The GOP Presidential Candidates

This was also adapted from the dance between Darcy and Elizabeth Bennet in BBC’s Pride and Prejudice miniseries.

2. George W. Bush and the Easter Bunny

Chip Somodevilla/Getty

For those you you taking issue with the fact that this photo has a place on this list, you are wrong. The land of the bunnies is ruled by a hereditary monarchy. For those of you who take issue with this photo because it is not awkward but instead shows true affection and trust between two leaders, you are probably right.

1. Obama and Castro (Again)

Of course this is No. 1. It is so painful. Castro clearly wanted a nice new picture showing off his BFF, only to be told by Obama that they aren’t actually best friends — in front of everyone he knows. It’s like Castro just awarded Obama the gold medal in the biathlon, but he’s so tired that he can’t even put his hand up. Or like Obama was in the middle of trying to pull the starving brain sucker joke before Castro pulled it away. The whole thing is made even more awkward by the fact that Obama is doing his “I am hiding the fact that this is the least fun thing I have ever done by smiling as much as possible” face. Don’t worry, Mr. President. You only have a few months of this left.