Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

Monica Lewinsky, a former White House intern who became embroiled in a dating scandal with Bill Clinton in the 1990s, revisited the episode during a public appearance on Thursday, April 23.

Clinton was 49 and serving as President of the United States in 1995 when he began a relationship with a 22-year-old Lewinsky. Their romance lasted 18 months.

When it became public in 1998, a furore ensued, with Lewinsky becoming fodder for late-night television jokes. Jay Leno especially targeted her on his eponymous talk show.

While Lewinsky initially laughed about being publicly humiliated on a grand stage, she went on to suggest that the reaction would have been different if she were a man. 

A question about the opportunity to change her past took Lewinsky back to the 1990s

Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

Image credits: Rodin Eckenroth/GA/Getty Images

Lewinsky spoke to a group of women at HSBC Bank’s The Financial Glow Up event at the 1 Hotel in West Hollywood this week.

“If you had to think about something that you would do differently now that you know what you know, what would that be?” someone from the audience asked.

Lewinsky raised her eyebrows before humorously clarifying if they were still “talking about finance,” because her answer could “cover a lot of different topics.”

She told the crowd she had to “be able to laugh” at herself in the grand scheme of things.

Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

Image credits: Gage Skidmore

In a separate question, Lewinsky was asked whether she had ever felt “wronged” in her life or cast as a “villain” for being a woman in a situation where a man would have been praised.

“I definitely feel that being a woman had so much to do with what my experience was. I think also being a woman who didn’t necessarily look like the person someone assumes would be in a situation like that,” she said.

Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

Image credits: Getty Images

Lewinsky added that she was not sure “if Jay Leno would have made as many jokes on late-night had I been a man.”

She penned an essay titled Shame and Survival for Vanity Fair in 2014 and launched her podcast Reclaiming with Monica Lewinsky in 2025 as part of an effort to reshape her public image.

Netizens leveraged Lewinsky’s media outputs, including her HSBC remarks, to accuse her of using the scandal to stay relevant

Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast
Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

Image credits: Clinton White House

“Just living off this affair for life. She’s no victim,” one said, while another asked, “Isn’t she tired of talking about this? It’s been 30 years. I wasn’t even born yet, and I’m tired of hearing about it.”

“When life gives you history, turn it into content,” a third remarked.

Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

Image credits: White House photo

“This is her only claim to fame, the only reason she gets any attention. She will drive that truck till the wheels fall off,” said a fourth.

“Hope she heals from the past instead of grandstanding it,” another user wrote.

Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast
Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

Not all comments were against Lewinsky, though. 

“She was a young girl at the White House. Clinton was the adult,” a user said, while another added, “A 50-year-old man and the frigging President of the United States was the true manipulator.”

“Clinton groomed her,” a third noted.

Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

Image credits: Reclaiming with Monica Lewinsky

Bill Clinton, during a televised White House event in January 1998, stated: “I did not have s**ual relations with that woman.”

In August of the same year, though, he confessed to having “inappropriate intimate contact” with Lewinsky.

Lewinsky, in a recent interview, said she believes Clinton “escaped” criticism while her life turned upside down

Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

Image credits: Kevin Dietsch/Getty Images

Speaking to The Times this February, Lewinsky revealed she contemplated taking her life because of the “excruciating” humiliation she faced after the affair became public.

While her personal fallout almost cost her her life, Lewinsky claimed that the consequences for the former president were not as severe.

Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast
Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

Lewinsky maintained that their relationship was consensual, however, Clinton misused his power and “escaped” accountability “a lot more” than she did.

While Lewinsky acknowledged her actions were “wrong” and that they “hurt people,” Clinton, in a 2018 appearance on NBC’s Today Show, appeared unapologetic.

“The American people, two-thirds of them, stayed with me. And I’ve tried to do a good job since with my life and my work. That’s all I have to say,” he said.

“Everyone has moved on except this poor soul,” a social media user said about Levinsky 

Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

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Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

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Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

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Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

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Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

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Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

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Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

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Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

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Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

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Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

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Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

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Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

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Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

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Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

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Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

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Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

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Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

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Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

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Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

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Monica Lewinsky Drops Unexpected Joke About Bill Clinton Affair And It Gets Awkward Fast

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