Chelsea Handler is not one to shy away from discussing any so-called taboo topics, including dating and sex.
“I’m not the marrying kind. I am not looking for children. I just want to have lots of love stories,” Handler exclusively told Us Weekly in a 2025 cover story. “I feel like that’s the most romantic way to look at love, and I’m glad I know that about myself because I think so many women are starting to be more open about [the fact that] this Prince Charming nonsense we’re sold is so silly.”
Months later, Handler stripped down to her birthday suit to deliver an impactful plea for men to get more vasectomies.
“As a woman with natural breasts, not that that has anything to do with this, it is time to explore vasectomies,” she said in a February 2026 social media video. “Since the beginning of time, women have been ducking and diving and dodging pregnancy face-first or Pikachu-first. Frankly, they’re exhausted.”
Handler thought that more men should get vasectomies as a form of birth control instead of putting the onus on women, especially when many people with the capacity to get pregnant are often left navigating painful Intrauterine Device (IUD) insertion procedures.
“Do you know how painful it is to get an IUD placed?” the comedian quipped. “It feels like a mouse trap in your uterus, and sometimes those things don’t even catch all the mice. You think I want to be an adult woman with acne or have mood swings, or get a period that’s so heavy it feels like the Hoover Dam just broke? I don’t.”
Keep scrolling for more of Handler’s candid comments about sex and dating:
A PSA for More Vasectomies
Chelsea Handler posed topless in a February 2026 Instagram video, pretending to give herself a mammogram. (A mammogram is a low-dose X-ray of breast tissue that can assist doctors in detecting and diagnosing breast cancer, according to the Cleveland Clinic.)
While undergoing her makeshift mammogram, Handler urged men to get vasectomies as a form of birth control.
“Women are tired of making concessions for men, especially in the bedroom,” she stated. “We have already been through enough letting you wear socks while you penetrate us. So man up, men, and if you can’t do that, enjoy the company of your hands. Vasectomies, one snip and that’s it.”
50 Cent ‘Convinced’ Her to Date
Chelsea Handler briefly dated rapper 50 Cent (real name Curtis Jackson) in 2011.
“He convinced me to date him after he was on my show,” Handler said on the “House Guest” podcast in December 2025. “It was like a Friday that he was a guest, I think. And then, I came in over the weekend, and there were like, dozens and dozens of roses in my office.”
She added, “All those guys used to hit on me, but Curtis was sweet.”
While Handler initially turned 50 Cent down, she did invite him to attend one of her comedy shows in New Orleans.
“We only dated for a very short time, but you know, people it blew up because people were like, ‘What are these two doing together?’” she recalled. “But he really was one of the sweetest people.”
What It’s Like Dating Multiple People
Chelsea Handler revealed in her February 2025 cover story for Us Weekly that she was having fun dating around after her split from fellow comedian Jo Koy.
“I’m dating. Dating is wonderful. Now, I understand what kind of date I am,” Handler told Us exclusively. “I want lovers all around the world. I want lovers all around the globe.”
Handler further admitted that she doesn’t thrive with dependency in romantic relationships and is open about practicing polyamory.
“I will be very honest and upfront with anyone who I’m dating, that you may not be the only one,” she said. “And if you need to know, I’ll let you know, but I’m just letting you know. Hopefully you don’t need to ask any further questions.”
She’s ‘A Free Spirit’
Chelsea Handler told Alex Cooper on a February 2025 episode of the “Call Her Daddy” podcast that wasn’t interested in ever getting married.
“I go through periods where I have multiple lovers. That’s kind of what I wanted to do when I was a little girl. I wanted to grow up and be a woman that did have multiple lovers,” Handler told Cooper. “I’m not interested in long-term commitments — to work, to people, to anything. I am a free spirit, and I want to remain and soar like an eagle. … I want to soar like an eagle with my heart and legs wide open.”
Proudly Childless by Choice
Chelsea Handler has long proclaimed that she has no interest in becoming a mother.
“There are millions of women just like me, but for some reason, every single one of us — at some point in our lives — is shamed by society for not wanting a baby,” Handler said on The Daily Show in 2023. “In America, and honestly everywhere, motherhood is treated as a woman’s essential purpose in life, as if our destiny is to let a tiny stranger rip a hole through our Pikachu from the inside out.”
While Handler admitted that she has “infinite respect” for moms, parenthood is difficult and she doesn’t have a desire to embrace it.
“When people ask me, ‘Do you have children?’ and I say no, they always look at me then and say, ‘Oh, I’m sorry,’ as if there’s something physically wrong with me,” she noted. “Instead of shaming childless women for what we’re doing to the country, you should be thanking us. We are saving society. We are more likely to give our money to charity, we have a lower carbon footprint [and] we’re the reason there are fewer screaming children on airplanes, in movie theaters and restaurants.”
