Chelsea Handler is dishing all the dirt surrounding her relationships with famous men.

In a recent interview on Kristin Cavallari’s podcast, “Let’s Be Honest,” the 51-year-old comedian shared she once went on a date with an unnamed famous A-List actor, noting “he was so boring.”

“We were flirting, and then I made the move,” she explained. “So I made the move, and he was receptive, and we were hanging out, and I saw him, and we went on a date, and it was unbearable. And I worked hard.”

She went on to explain that part of the problem was that “he was so serious about himself as an actor” and spent a lot of time “talking about acting in a way I can’t take seriously.”

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Handler said that “he was very much about himself and his process and his acting,” and after carving out time in her schedule to meet with him while abroad, Handler ended the date disappointed with the outcome, saying “he didn’t ask me one question about myself.”

“I felt like I was 25 years old and had to like make up a lie you know to get away cause I had really pursued him, but then so once I sat down with him I was like no,” she said. “Immediately I was like you’re so boring and you’re so annoying – like anyone who talks about themselves for that long on a date is just that’s exactly what’s wrong with men.”

Earlier in the interview she also shared that she “had a nice little affair” with a well-known celebrity for a few months, but also refused to name that star.

During a recent appearance on the “Howie Mandel Does Stuff” podcast, Handler commented on the current dating culture, noting, “It’s very hard in today’s world to meet straight guys that have their s— together.”

“So, I was initially trying to help straight women meet straight men,” she explained. “But I think with dating apps and social media, there’s just so much abundance and so much choice that nobody really feels like they have to … lock it in.”

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When speaking about her own love life, Handler told the “Not Skinny But Not Fat” podcast in January that she “love[s] all drugs,” and whoever she dates needs to as well.

Handler then went on to explain that she and her friends often gather at parties and measure out the different drugs. When asked if she could be friends or date someone who is sober, Handler says she tries not to.

“No. Like if I’m gonna date a guy, they’re gonna have to party,” she said. “I wanna party. I like to get loose. And by the way, I’m 50 years old. Years. Years. I’m a perfect shining example of drugs being an enhancement to my life. Yeah. Like what, what are you gonna say? I’m a mess. I’m a loser. I don’t have it together? I do.”

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Most recently, Handler was in a public relationship with comedian Jo Koy, who she dated for around one year from 2021 to 2022, telling the “Now What?” podcast in December 2022 she decided to end the relationship after “it just became clear that this was not my person.”

While she is currently dating someone, the former “Chelsea Lately” host said on the “Angie Martinez IRL Podcast,” that she thinks marriage is “outdated” and that she prioritizes her freedom.

“I’m here for women, and I’m here for myself,” she said. “I’ve never been very thirsty for a man or a partner. You’ve got to really kind of get my attention for me to pay attention in a serious way, because otherwise it’s a bunch of casual encounters. You know what I mean? I like that. I like traveling a lot. I like hooking up with guys. I don’t like to get too serious. I don’t want someone in my space all the time. I just am not interested in that.”

A social media post asking for “peak woke” moments over the years quickly went viral over the weekend as people posted older clips of Sen. Bernie Sanders, I-Vt., being interrupted at a Black Lives Matter rally in 2015, a transgender swimmer winning a women’s NCAA title and a “choose your fighter” video featuring “Squad” member Rep. Alexandria Ocasio-Cortez.

Ocasio-Cortez, along with other Democrats including Reps. Jasmine Crockett, Lauren Underwood, Katherine Clark, Judy Chu and Susie Lee, participated in the TikTok “choose your fighter” video trend last year.

The video went viral and was mocked across both sides of the aisle in March 2025.

Outkick’s Clay Travis flagged Lia Thomas, a transgender swimmer’s NCAA swimming title in 2022, in addition to two ESPN announcers holding a moment of silence to protest a Florida bill dubbed by critics as the “Don’t Say Gay” bill, as reported by Yahoo! Sports at the time.

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Many also pointed to videos related to the COVID-19 pandemic, including one of former Chicago Mayor Lori Lightfoot dressed in a “Rona Destroyer” costume in 2020.

Another social media user posted a clip of former New York City Mayor Bill de Blasio announcing announcing that people could get free Shake Shack fries if they got vaccinated during a daily press briefing in May 2021. The promotion also included a voucher for a Shake Shack burger.

In the video, he says, “I want you to look at this and think about — again, some people love hamburgers, some don’t. We really want to respect all ways of life — but if this is appealing to you, just think of this when you think of vaccination.”

After taking a bite of the burger on camera, De Blasio says, “Vaccination. Mmm. I’m getting a very good feeling about vaccination right this moment.”

Townhall’s Siraj Hashmi wrote in response, “Billy Porter performing ‘For What It’s Worth’ at the 2020 Dem Convention when everything was virtual because of COVID and the ashes from the George Floyd riots were still smoldering is PEAK WOKE.”

Hashmi also pointed to a COVID-related video of celebrities singing John Lennon’s “Imagine” in March of 2020.

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Gal Gadot, along with other celebrities including Kristen Wiig, James Marsden and Natalie Portman, posted a cover of John Lennon’s famous song “Imagine” on social media in an effort to inspire hope.

A user pointed to a clip of Bernie Sanders being disrupted at a 2016 campaign event by Black Lives Matter protesters.

Two women walked up to the podium where Sanders was speaking and demanded the microphone as one shouted, “We are angry,” according to NBC News.

After receiving boos from the crowd, one of the women said, “I was going to tell Bernie how racist this city is … but you already did it for me.”

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The “End Wokeness” account, that posed the “peak woke” question originally, posted a video of White people kneeling and asking for forgiveness from the Black community.

The viral moment took place in Houston in 2020 after the death of George Floyd.