Jimmy Kimmel had a rather embarrassing experience when he first met former First Lady Michelle Obama. During an appearance on *The Ellen Show* in 2018, Ellen DeGeneres reminded him of a particularly awkward moment involving a tight ice-skating dress. Kimmel, who was on the show as a guest, recounted the story of how he ended up meeting Obama while wearing the costume, which wasn’t exactly the ideal outfit for such an occasion.
The incident took place when Kimmel was preparing a birthday surprise for Ellen, who was turning 60 at the time. As part of the surprise, Kimmel dressed up in an ice-skating outfit complete with skates and all the necessary gear. The costume was meant to be funny and lighthearted, fitting the celebratory mood of the show. However, things took an unexpected turn when Kimmel was informed that Michelle Obama was waiting backstage and wanted to greet him before her segment on the show.
Kimmel described the moment as one of the most embarrassing experiences of his life. He explained that he had no choice but to meet Obama in the ridiculous outfit, which left very little to the imagination. Reflecting on the incident, Kimmel jokingly expressed how mortified he was, saying, “Top five most embarrassing moments of my life. That was bad. That was really bad. I feel like I should be deported for that.” His comments, as reported by *Vanity Fair*, highlighted just how uncomfortable he felt at that moment.
Despite the awkwardness of the situation, it seems that Kimmel didn’t need to worry too much about what Obama might have thought of him. Michelle Obama is known for her great sense of humor, and she has shown that she can take a joke just as well as she can dish one out. In fact, she later appeared on Kimmel’s own show, *Jimmy Kimmel Live*, in 2021, where the two discussed various topics, including life during quarantine, their daughters, and even more personal matters.
During the interview, Kimmel asked Michelle Obama a rather bold and unexpected question about a significant historical event. He inquired whether she and her husband, former President Barack Obama, had celebrated the night that Seal Team 6 took out Osama Bin Laden by making love. The question caught Michelle off guard, but she quickly turned the tables on Kimmel, delivering a sharp and humorous response. She teased Kimmel, saying, “You know, I have to tell your audience that for some very sick reason, you’re very obsessed with this question of that major historical event.”
Michelle Obama didn’t stop there. She continued to poke fun at Kimmel, comparing his curiosity to that of a young boy sneaking a peek at something he shouldn’t be. “You’re still that little boy in your bedroom under the cover with the flashlight going, I hope nobody sees me,” she joked, mimicking the act of flipping through a Playboy magazine. Her playful roasting of Kimmel was well-received, showcasing her quick wit and ability to handle even the most awkward of questions with grace.
This wasn’t the only time Kimmel found himself in a humorous exchange with Michelle Obama. The comedian has interviewed her multiple times on his show and has encountered her at various events. Their interactions have always been light-hearted and filled with banter. Kimmel even took part in a social media trend called the #PromChallenge, where people were encouraged to share their prom photos. Michelle Obama participated by sharing a throwback photo of herself in a pink satin, polka-dotted dress from her prom night.
Kimmel, staying true to his comedic nature, responded with a humorous post of his own. He shared that he never attended prom, homecoming, or any similar event, but joked that his friend (and now bandleader) Cleto Escobedo III let him “sleep with him that night anyway.” This playful interaction on social media further demonstrated the friendly and teasing relationship between Kimmel and the former First Lady.
In summary, Jimmy Kimmel’s initial encounter with Michelle Obama might not have been the smoothest, but it ultimately led to a series of amusing and memorable interactions between the comedian and the former First Lady. Their exchanges, both on and off-screen, have highlighted Michelle Obama’s sharp sense of humor and Kimmel’s ability to laugh at himself, making for entertaining television and a fun dynamic between the two.
