Michelle Obama does not have a clean track record when it comes to her share of awkward public moments. Not just during her tenure as the U.S. First Lady, she has, in fact, made some widely shared moments on-camera, which have left the internet in a hilarious riot.
Before diving into the pool of awkward moments to her name, one must note that most of these have occurred during many of her public interactions. From dealing with the Trumps to foreign dignitaries or even heckling interviewers, there has been a lot that has gone under the category.
While she may have been popularized as an image of poise, it has been these very surprising viral moments of Michelle Obama that have challenged her image, to say the least.
One of the first memories on the subject matter is definitely Michelle and Melania Trump’s unusual encounter with a Tiffany box. On Donald Trump’s swearing-in as the 45th U.S. President, the Obamas were tasked with welcoming their successors to the White House. And Melania, being the gracious guest-turned-new occupant, did not forget to present a Tiffany gift box to Michelle.
What could have been a perfectly off-radar and simple moment became viral in no time, all thanks to Mrs. Obama’s bewildered expression seeing the box itself. Barack became the saving grace for the remainder of the moment, as he carried the box.
The 61-year-old later talked about it on Ellen DeGeneres’ talk show, offering a play-by-play of what really happened back then. In her words, “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]?”
Tiffany blue box…
Melania Trump’s Inauguration gift to Michelle Obama January 20, 2017. pic.twitter.com/GKPQ0NZrXZ
— LIT (@IgniteTruth) March 1, 2025
Talk about those moments when funny turns cringe? Michelle Obama landed in one such incident when she had an awkward exchange with Ellen DeGeneres on the latter’s show. The pair made a visit to CVS Pharmacy, where they shopped for a list of different items. Allegedly, Michelle picked stuff that was regularly needed by her family.
Obama’s chat with Ellen grabbed attention when she started teasing the show’s host with statements like “Can you chill out!” and “This is not how you behave!”
Once Michelle began paying for the items, DeGeneres asked a silly question about whether she could have her face printed on currency notes. Michelle’s quick reply was unexpected when she said, “You would’ve had to have done something grand like Harriet Tubman. You should have freed some slaves.”
The awkward encounter ended when Ellen and Obama stepped out of the store, and the latter claimed the whole experience was like “taking a 3-year-old to the store.”
Remember when Michelle Obama and Ellen DeGeneres went to CVS and Michelle still chose to strictly adhere to the laws of our government?
We’ve fallen so far from grace. #RuleOfLaw #QuidProQuo #ImpeachAndRemove #QuidProQuoTrumpsGottaGo #TrumpImpeachment pic.twitter.com/1wvSPW3stU
— Adrian (@Yo_AdrianG) October 22, 2019
For one reason alone, Donald Trump’s swearing-in captured some of the most awkward on-camera moments of Michelle Obama. Besides the Tiffany box encounter, there was a time when she quite evidently appeared to show her disdain towards the 79-year-old who succeeded her husband Barack as the next U.S. President.
From a definite side-eye roll to abruptly stopping her smile, there was a lot for the internet to digest. Speaking with ABC News later, Michelle confirmed that she indeed “stopped even trying to smile” throughout the rest of the inauguration day, signalling her feelings against Donald Trump. A few more years later, in 2020, Michelle Obama’s viral Instagram post in 2020 gave it all away.
She had revealed, “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. 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.”
Former first lady Michelle Obama will not attend Donald Trump’s inauguration next week, her office confirmed Tuesday. pic.twitter.com/CJ3IUoYogV
— Republicans against Trump (@RpsAgainstTrump) January 14, 2025
Besides politically driven animosity, there has also been a time when Michelle Obama navigated her command through a loud audience. Claiming her authority on the spot, she made some awkward comment on stage, but it did help Michelle regain her presence on stage.
At a New Haven event, Michelle met with one of the most riled-up audiences who were in no mood to listen to her. Things went off the rails pretty soon when a woman shouted and called her a dreamer. The former First Lady replied, “OK, I’m going to wait and let you finish. I hear every word you are saying.” The crowd again tried to throw her off with their hoots.
This time, Michelle took a firm stand on the matter and said, “You guys are lively here. New Haven, you are all fired up. You guys want this to be a participatory rally? Who else should I have come on stage?”
Call it awkward or bold, it did take a lot of guts for someone to take center stage and deliver a speech where the audience is not ready to listen.
