Chelsea Handler Reveals Why She No Longer Dates Older Men After Turning 50

Chelsea Handler is sharing new details about her personal life, from her evolving dating preferences to unexpected moments from her past. The Chelsea Handler Reveals Why She No Longer Dates Older Men After Turning 50 first appeared on The Blast

Chelsea Handler is sharing new details about her personal life, from her evolving dating preferences to unexpected moments from her past.

During an appearance on “The View,” she addressed her new relationship and why she’s now dating younger men.

Chelsea Handler also recently opened up about a troubling experience with a home she purchased years ago.

Chelsea Handler Says Turning 50 Inspired Her To Date Younger Men

During a March 25 appearance on “The View,” Chelsea Handler opened up about her dating life and why she’s recently shifted her focus to younger men.

The 51-year-old comedian addressed her relationship after the hosts, including Whoopi Goldberg and guest co-host Abby Huntsman, brought up her recent “hard launch” on social media. Handler, however, saw it differently.

“You said I hard-launched a relationship. I felt like that was a soft launch,” Handler joked, explaining that she had subtly included photos of her new partner in Instagram posts rather than putting him front and center. “I wasn’t proclaiming I was in love or this was my boyfriend.”

Handler then shared that her new relationship is already longer than many of her past ones.

“He’s 37 years old,” the comedian noted, per People Magazine. “I’ve always dated older guys, but then I turned 50, I’m like, ‘I think I’m going to go back the other way.'”

How The Comedian And Her New Boyfriend Met

Handler and her new man reportedly met in November at a blackjack table inside The Cosmopolitan in Las Vegas.

The comedian recalled boldly asking him to lend her $1,000 while he was winning big.

He agreed without hesitation, and that spontaneous moment sparked their connection. Though Handler playfully calls her younger partner “Cowboy,” she has kept his identity private.

Their relationship quickly turned adventurous. After reconnecting, he joined Handler on a Thanksgiving trip to Antarctica, and the two have since traveled together to places like Istanbul, Jamaica, and Finland.

Chelsea Handler Details Whirlwind Romance And Upcoming Tour

Handler first hinted at the romance earlier this month through social media posts, and she later shared more details during an appearance on “Jimmy Kimmel Live!”

She recalled how he texted her after they met, calling the comedian “a vibe” and expressing interest in seeing her again, even agreeing to meet her in Antarctica.

Before this, Handler was in a relationship with fellow comedian Jo Koy, which ended in July 2022.

As she embraces this new chapter personally, Handler is also staying busy professionally.

Her latest comedy tour kicks off March 27 in Portland and will take her across multiple cities in North America before wrapping up on December 6 in Vancouver.

The Comedian Recalls Childhood Lie About Goldie Hawn That Boosted Her Popularity

Meanwhile, Handler once admitted to spinning a bold childhood lie about Goldie Hawn, and it paid off.

While hosting a gala in Hawn’s honor, Handler shared that back in third grade, she told classmates she had been chosen to play Hawn’s daughter in a sequel to “Private Benjamin.”

The story wasn’t true, but it quickly boosted her popularity at school. According to an insider at the event, her peers fully believed the claim, treating her like royalty and even nominating her as a Girl Scout troop leader.

Handler later joked that she eventually found a way into Hawn’s real-life circle. She humorously said she “single white female’d” her way in after befriending Hawn’s longtime partner, Kurt Russell, adding that she now feels like they’re her “real parents.”

Chelsea Handler Says ‘Toxic’ L.A. Home Bought From Robert F. Kennedy Jr. Left Unlivable For Years

Speaking on a March 5 episode of her podcast, “Dear Chelsea,” Handler alleged that a property she purchased from Cheryl Hines and her husband, RFK Jr., was in such poor shape that she has yet to move in five years after buying it.

She explained that the sale was conducted privately through trusts, so she initially didn’t realize who the sellers were.

Describing the house as “toxic,” Handler claimed inspectors warned her the environment was unsafe to live in for an extended period after the purchase.

Handler also expressed disbelief that Robert F. Kennedy Jr., who is the secretary of the U.S Department of Health and Human Services, would have maintained a home in such condition.

According to Handler, once the property was fully examined, it became clear that the issues were far worse than expected, with inspectors telling her she “cannot live here for at least two years.”

However, during a March 17 appearance on “Jimmy Kimmel Live!” Handler claimed that she had finally moved into the “toxic” home.

The Chelsea Handler Reveals Why She No Longer Dates Older Men After Turning 50 first appeared on The Blast