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Awkward Michelle Obama Moments Captured By Millions

Even Michelle Obama has awkward moments. The former First Lady spent over a decade in the public eye: during her time on her husband’s first presidential campaign, the years spent in the White House, and her time after leaving Pennsylvania Avenue. All the while, Obama captured the hearts of many — and subsequently had a lot of her life captured on camera.

The White House and its occupants always seems to come under intense scrutiny and immense public interest, and the Obama White House was no exception. Obama was just as beloved as she was criticized — everything from her hair to her outfit choices to her legal acumen was questioned, and because of that, she learned how to maneuver with a lot of grace.

Even so, there have been a handful of awkward moments captured by millions involving the former First Lady. Many have had to do with the Trumps, which doesn’t come as a huge surprise, and others have been tense encounters with hecklers and interviewers. While Obama may be the picture of perfect poise, she still fell victim to some less than cute, often viral moments. Here are the awkward Michelle Obama moments captured by millions.

Michelle Obama's Tiffany Box moment with Melania Trump was so awkward

It was the exchange seen around the world. The day that Donald Trump was sworn in as 45th president of the United States gave us so many awkward exchanges, but none were as bad as the Tiffany box incident. As the Obamas welcomed the Trumps to the White House, Melania Trump handed Michelle Obama a gift, and as noted by magazine, the exchange went viral “thanks to Obama’s somewhat flummoxed facial expression.” 

Speaking about the awkward encounter after the fact on The Ellen Show, Michelle said that the gift was unexpected, and as such, she didn’t know what to do with it. “What am I supposed to do with this gift? And everyone cleared out and no one would come and take the box. And I’m thinking, Do we take the picture with [it]?” she recalled. 

Fortunately, Barack Obama saved the day, when he took the box and brought it inside. But before her husband could swoop in and save the day, the awkward moment was already captured on camera.

Michelle Obama's outing with Ellen DeGeneres was so funny… until it got a little awkward

After allegations of workplace hostility came to light, people have been watching Ellen DeGeneres’ show with a changed perspective. So it comes as no surprise that this awkward exchange between DeGeneres and Michelle Obama hits a little different now. The pair made a trip to CVS Pharmacy, and it was hysterical watching Obama and DeGeneres go around the store and pick out different items that the First Family needed, until it wasn’t. 

Obama started saying things like “Can you chill out,” and “This is not how you behave!” Then when she started to pay for the items, DeGeneres if she could get her face on a bill, and Obama said no. “You would’ve had to have done something grand like Harriet Tubman,” Obama said. “You should have freed some slaves.” 

Things then got even more awkward when Obama concluded their trip to CVS by saying, “It’s like taking a three year old to the store.” The whole trip was a viral bit and most of it was funny, but it got to a point where we really couldn’t tell if Obama was kidding or not.

Michelle Obama was seen shaking her head in disappointment during this awkward moment

Politics can often be a rough arena, but things got really awkward when Representative Joe Wilson interrupted then-President Barack Obama during an address to Congress. As noted by The Wall Street Journal, President Obama started to discuss legislation regarding health care, and made the point of saying that it would not be provided to undocumented immigrants. Cue Joe Wilson, who screamed “You lie!” at the President. 

And if things weren’t already tense, Michelle Obama was visibly seen “shaking her head from side to side” in response. The former First Lady, who pursed her lips in disappointment, was not alone. House Speaker Nancy Pelosi quickly turned to give Wilson a dirty look, and then-Vice President Joe Biden later went on Good Morning America to address the situation. “I was embarrassed for the chamber and a Congress I love,” Biden said, as noted by The Goshen News. ”It demeaned the institution.” 

Up until that moment in 2009, Michelle Obama wasn’t known for expressing her disdain for political opponents, but this awkward moment really changed the course.

Melania Trump didn't reach out to Michelle Obama for advice… and the fallout was awkward

The First Lady is a difficult role to fill, and many have relied on their predecessor for advice. Melania Trump, though, didn’t reach out to Michelle Obama, and the fallout was awkward. 

Obama was asked by Robin Roberts about her thoughts on Trump and her work as First Lady during a CNN interview after her time in the White House. Obama didn’t comment, saying that she wouldn’t judge the current occupant of the role. But when pressed a bit further, Obama admitted that Trump hadn’t reached out to her for advice, another First Lady tradition Melania Trump refused to do. 

Additionally, when Obama became First Lady, Laura Bush made herself available to her. As such, Obama extended the same courtesy to Trump. “Has she reached out to you?” Roberts asked. “No. No she hasn’t,” Obama responded, the tone of her response riddled with tension. Trump’s office responded, saying that “Mrs. Trump is a strong and independent woman who has been navigating her role as First Lady in her own way,” a snub to the olive branch extended by the former first lady.

Michelle Obama's side-eye during Donald Trump's inauguration was seen around the world

Donald Trump’s inauguration gave so many awkward moments, but Michelle Obama’s side-eye pretty much stole the show. Early on in the day, it was clear that Obama was trying to be gracious, but as things progressed, so did the her tense disdain for her husband’s successor. She later shared with ABC News that she “stopped even trying to smile” during the day’s festivities, something that was very clear when Trump took to the stage for the oath of office and his inaugural address. 

Obama kept the lid on her thoughts about the awkward exchanges between herself and the Trumps, but eventually she did share what she was thinking on Instagram in 2020. “I’ve been reflecting a lot on where I was four years ago… I have to be honest and say that none of this was easy for me,” she confessed. “Donald Trump had spread racist lies about my husband that had put my family in danger. That wasn’t something I was ready to forgive.” Now the expression she made throughout the inauguration day in 2016 make so much more sense.

In an awkward slip-up, Michelle Obama didn't know who to greet first

President Barack Obama’s inauguration day gave onlookers an awkward Michelle Obama slip-up that was far more endearing than the Trump inauguration, but nevertheless, Michelle did trip up just a tad when greeting President George Bush and First Lady Laura Bush. In a video captured by the Associated Press, Michelle can be seen reaching for President Bush’s hand to shake, then quickly realizing that she should have greeted the First Lady. The quick little gaffe was a bit awkward, but if anything, very reflective of the nervous young couple that was about to occupy the White House. 

But for those of you that are political junkies, you know that the 2009 transfer of power was not the last time the two couples would be seen together. Public event after public event, the bond between the Bush and Obama families became more and more apparent, and basically culminated when Michelle wrapped her arms around George during the opening of the National Museum of African American History and Culture. We love to see it.

Michelle Obama awkwardly navigated hecklers and an overly loud audience

One event in New Haven had such a fired-up crowd that it got the best of Michelle Obama’s speech. As noted by the New Haven Register, Obama was addressing the crowd, expressing her support for Governor Dannel P. Malloy. But things went off the rails when people started yelling at Obama from the audience. 

First, a woman shouted at Obama, telling her that she was a “dreamer,” and started expressing her concerns about being deported. Obama ended up saying, “OK, I’m going to wait and let you finish. I hear every word you are saying.” The crowd again threw Obama off just a bit as they kept talking back to her, and she ended up addressing their spirited pleas head-on. “You guys are lively here. New Haven, you are all fired up. You guys want this to be a participatory rally?” she said. “Who else should I have come on stage?” 

In the end, Obama handled the rowdy crowd like a champ, but it’s a little awkward when you go to speak to an audience that just wants to interrupt.

This body language expert broke down the awkward first meeting between Michelle Obama and Melania Trump

The transition between the Obamas and the Trumps was filled with tension, and things were especially awkward when Melania Trump was invited to the White House to sit down with Michelle Obama. Body language expert Elizabeth Kuhnke broke down the meeting between the two women for the Telegraph“At the White House, [Melania] seems like a girl who has been called into the headteacher’s office: she looks nervous, her body is contained and she is holding everything in,” Kuhnke explained. “Melania’s mouth is held tightly together, she is keeping quiet, rather than risk getting it wrong again.” She added that this conforms to the role she’s supposed to play: “beautiful and passive.” 

So what, in contrast, was Obama’s stance during the awkward meeting? Well, Kuhnke revealed that “Melania is a guest in Michelle Obama’s environment and it shows.” And although Obama’s facial expression were a little forced and over-animated, Kuhnke said that she used the meeting to signal to “Melania that this is her home and she is in control.” It was awkward, it was tense, and it was definitely a power struggle.

Michelle Obama knew how to throw some shade when asked about Melania Trump's copycat speech

The tension between Michelle Obama — who’s undergone a stunning transformation — and Melania Trump has always been pretty palpable, and things got really awkward when Trump used large portions of an address that Obama gave in 2008 in her own controversial speech during the Republican National Convention in 2016. The speeches, which can be seen side-by-side here, are eerily similar. As such, Trump came under a lot of fire for copying such large portions of the former First Lady’s address, and eventually blamed a speech writer for the error. 

But the awkward damage was already done; Obama was asked about the gaffe during an appearance on The Late Show with Stephen Colbert. “Melania Trump was criticized for using what turned out to be a portion of your speech… [Are you] sympathetic for what happened to her?” Colbert asked. “Yeah, that was tough,” Obama responded with a terse smile, and a slightly awkward and impactful pause followed. Colbert got the hint and followed-up with a “Let’s move on,” because the tension in the room was palpable.

Michelle Obama looked seriously stressed out at this memorial service

Memorial services for world leaders seem like they’d be pretty somber, but when Michelle and Barack Obama attended the service for renowned leader Nelson Mandela, she looked less than amused — in part due to her husband’s attention towards Gucci Helle, the prime minister of Denmark. At the event, the Obamas were sitting next to Helle, and perhaps the first act that President Obama did that annoyed the First Lady was when he took a selfie with Helle and Prime Minister David Cameron. 

Things escalated when the President appeared to say something funny, because as he shared a laugh with Helle, Michelle looked less than thrilled. As the memorial progressed, President Obama kept leaning towards Helle to share his thoughts, all while his wife was sitting next to him. As reported by The Atlantic, “After President Obama left … Michelle Obama saw the opportunity to pull off the switch,” and ended up stealing her husband’s seat, perhaps to dull the obvious attention that the two were giving each other.” Talk about awkward. No wonder Michelle Obama isn’t a fan of politics.

Michelle Obama served some serious shade during this event in Washington D.C.

Any time that Barack and Michelle Obama interact with the Trumps is bound to be icy, but this exchange between Michelle and Donald Trump was so awkward, even for them. During the state funeral of George H.W. Bush, the tension was apparent between the 45th president and the former First Lady. 

At the event, Michelle watched as Donald and Melania Trump took their seats at the Washington National Cathedral. Donald greeted Barack, and after what felt like a significant pause, extended his hand to Michelle. The former First Lady “raised her eyebrows and shook the 45th president’s hand herself. But she did not look thrilled,” according to Newsweek. 

The tense encounter can be seen on YouTube, and people in the comments clearly picked up on the nature of the whole interaction. “I wonder if that was awkward,” one user wrote. “You could just feel and see the tension between them and the Trumps,” wrote another. It probably didn’t help things given that Donald’s former political rival, Hillary Clinton, was sitting just down the pew. The awkward tension was just overflowing at that point. 

Things went downhill quickly when a heckler threw Michelle Obama off during a speech

It’s pretty uncommon to see Michelle Obama lose her cool, but she was not having it during this event in 2013. As noted by NPR, Obama was speaking during an evening Democratic Party fundraising event in Washington D.C. when a heckler began shouting at her — and things went downhill from there. “One of the things that I don’t do well is this,” Obama said to the protestor, who turned out to be Ellen Sturtz from the GetEQUAL campaign. “Do you understand?” 

Obama then moved over to Sturtz and said, “Listen to me or you can take the mic, but I’m leaving. You all decide. You have one choice.” The very rare interaction between Obama and the critic ended with Sturtz being escorted away from the event, with people in attendance shouting things at Sturtz such as “you need to go!” Sturtz later told The Washington Post that she was “taken aback” by the whole ordeal, saying that the former First Lady “came right down in [her] face.” If one thing is clear from this, don’t mess with Michelle Obama.

After an awkward pause, Michelle Obama finally answered this question

While sitting in Ellen DeGeneres’s “hot seat,” Michelle Obama avoided answering a pretty awkward question. “Tell us something you stole from the White House,” DeGeneres said, and a slight look of shock appeared on Obama’s face. After a long pause and some awkward giggles from the audience, Obama responded. “We had to pay for everything,” she said. “That’s in the book.” 

The book in question was Michelle Obama’s autobiography Becoming, and due to its release, she made many media appearances. “I know you stole stuff,” Obama said to DeGeneres after the question was posed to her. “I did,” DeGeneres said. “I stole the napkins that were in the bathroom.”

When asked if DeGeneres still had the contraband, the host said no. “What did you do with them?” Obama asked with a more stern expression than not. “I don’t know,” DeGeneres said, and the bit went on from there. It was hard to tell if Obama was actually mad at the line of questioning, or whether the exchange was just awkward. You can tell for yourself by watching it here.

The dynamic between Michelle Obama and these international dignitaries was so awkward

Cultural norms are usually observed by the President and First Lady while traveling on behalf of the United States, so things got really tense when Michelle Obama chose not to wear a head covering while in Saudi Arabia. According to the Telegraph, Obama “dressed conservatively in black trousers and a long jacket, wearing loose clothing that fully covered her arms, but did not cover her head.” As such, the internet lost its mind. 

For those not aware of how big of a deal the choice was, it’s required that all Saudi women cover their heads in public. As such, many took to social media to express their disdain for Obama’s choice. As noted by The Washington Post, “More than 1,500 tweets using the hashtag #Michelle_Obama_unveiled” were made in the aftermath of the interaction.” And if that wasn’t awkward enough, the body language between Obama and the male Saudi delegation was really charged because “the simple act of not covering your head can be political, intentionally or not.”

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