Who’s been on Chelsea (Love) lately?
The comedian has been candid about his short-lived relationships over the years, insisting to Kristin Cavallari on a May 2026 podcast episode that he’s “not a commitment phobe.”
At the time, the Daytime Emmy Award winner told “Let’s Be Honest” listeners, “I’m never too late to a party. I know when to end things. … My life is so sweet and wonderful. I just don’t want it to get in the way.”
The former “Chelsea Lately” host said that “if you’re really in love, there’s nothing wrong with being faithful for five or six months or even two years,” but once things get “locked up,” she’s “out.”
Handler made it clear that she’s “not scared,” adding that she’s not spending her single life “desperating and hoping to meet someone.”
Page Six reconsiders her relationships and loves, from rapper 50 Cent to celebrity chef Bobby Flay.
Ted Herbert
In a roundtable discussion in May 2026, Handler said her longest relationship was four years, citing her time with Comcast CEO Ted Herbert.
More than 10 years after the duo split in 2010, Handler has revealed the threesome he had with a female masseuse that led to their split.
“I became very interested in this woman (and)…I ended up having several relationships with her without the man,” she said on “Radio Andy” in 2023. “That’s when I knew it was time to break up with him.”
Handler previously blamed work for the end of their relationship, telling Marie Claire in 2012, “I’d come home from work and Ted would be like, ‘Do you want to watch your show?'” You’d say, “No, I just got back from a show.” That’s the last thing I want to do. ”In the end, that was the reason it didn’t work out. ”
Dave Salmoni
Handler and Animal Planet star Dave Salmoni started dating in 2010, and she revealed their breakup in her “Chelsea Lately” monologue.
“Up until a few weeks ago, I was working very closely with Animal Planet, but unfortunately that contract was terminated,” she joked.
“But I enjoyed being in bed with them, so I might get involved in a project from time to time,” Handler added.
50 cents
Handler previously referred to 50 Cent, whom she dated in 2011, as her “favorite ex-boyfriend,” but retracted that title when she endorsed Donald Trump for president in 2020.
However, she gushed about her “boyfriend” in a January 2023 interview with Entertainment Tonight, calling him “fun to be around.”
“My friends loved spending time with him, and I loved spending time with him, too. It was a pretty short-lived romance, only two months. But if I met him, I would definitely have drinks with him.”
The former couple started dating after the Grammy winner sent Handler “dozens of roses,” she told listeners of her “House Guest” podcast in December 2025.
Andre Barras
The couple dated handler and businessman Andre Barras from 2011 to 2013.
The romance “knocked the wind out” of the actress and “drained her,” she confessed on Marc Maron’s podcast “WTF” in 2012.
“It took a lot of time and it was really, really hard to concentrate on anything. He lives in New York and I live in Los Angeles, and it was constant back and forth of getting on planes and seeing each other. … It was just exhausting.”
Handler later characterized the romance as “toxic” in February 2025’s Call Her Daddy, claiming that it made him “paranoid…the worst version of himself.”
Without disclosing Balazs’ name, she detailed her wild behavior before their breakup, saying, “I had him plant 17 (trees) on both sides of his driveway. … Every fall and spring, I get an email from him saying, ‘I can’t believe I lost you. Would you like to come see your tree?'” And I said, “I’m not interested.” ”
Joe Koy
Page Six broke the news in 2021 that Handler and fellow comedian Jo Koy were dating after 20 years of friendship, but the two announced their split the following July.
The former Chelsea presenter said on the Armchair Expert podcast in 2025 that he had “no choice” but to quit because it would “compromise[his]values”.
Handler explained, “There were a few times where it was clear that we had different ideas about being together, spending time together, and his expectations of me as his girlfriend. To me, that was very old-fashioned and old-fashioned and just didn’t work.”
“I never doubted[my]decision for a second,” she said, clarifying that she ended her relationship with Coy in a “vulnerable, mature (and) healthy way.”
Bobby Flay
Handler accused Frey of being “cheesy” while describing his only “bad” date with Cavallari in May 2026.
Not only did Handler infuriate the “poor” restaurateur for once sending room service to her hotel room and leaving her the bill after they “talked” and “flirted,” he also watered down the date.
“I was like, I messed up,” she declared, insisting that Frey was not her “mate.”
Joe Ragula
Handler’s new romance began in earnest in March 2026, when it was revealed that her boyfriend was Joe Ragula, a construction company executive.
The two met at a blackjack table in Las Vegas in November 2025 and quickly took their romance to the next level with a trip to Antarctica.
“I’m still going to get along with this guy,” she told the Las Vegas Review-Journal. “It’s hot and women like me need big moves like that.”
mysterious men
On 2026’s “Let’s Be Honest,” Handler declined to identify the “serious” but “self-righteous” actor who spent the entire date talking about himself, and teased “a nice little thing” with another mystery A-lister.
She also played a mother in 2025’s Call Her Daddy as she describes the new man in her life, “respecting his privacy.”
Handler said: “We actually became lovers about six or seven months ago. I invited him to Mallorca on a trip with a group of friends. … I’ve known him for years. I’ve always been attracted to him, but he just wasn’t available. I always wanted someone like him in my life.”
