NEWSChelsea Handler, 51, Wants Nothing More Than a 'Good Sexy Affair' as Comedian Ditches 'Long-Term' Relationships in Steamy Confession
Chelsea Handler opened up about her dating outlook.
May 27 2026, Published 3:40 p.m. ET
Chelsea Handler got candid about dating, revealing she prefers casual flings over serious relationships.
"I am not a long-term person," Handler, 51, admitted during the Tuesday, May 26, appearance on the "Let's Be Honest With Kristin Cavallari" podcast. "I just am not interested in anything that comes after the six-month mark. I’m not interested in dealing with your family or issues."
Chelsea Handler Would Rather Have Steamy Affair Over Long-Term Relationships
Chelsea Handler isn't interested in 'being part of a unit' when it comes to relationships.
She confessed she may not have this mindset forever, but added, "I'm not in a place in my life where I wanna take on another person."
"I don't want to be part of a unit," she continued. "I want to have a good s--- affair."
Handler, who is known to be open about her love life, emphasized her focus was "having s-- and looking her best."
When asked if she was currently getting physical, the comedian responded, “Not in this moment, but I’m having s--, yes.”
Chelsea Handler spoke with Kristin Cavallari during an appearance on the latter's podcast.
It Goes Down in the DMs for Chelsea Handler
Chelsea Handler said she often responds to her direct messages on social media.
The Fun Size actress confessed many of her romantic encounters have come through her social media DMs, though she noted she typically only responds to men with whom she already has some familiarity.
Handler also gave rare insight into her most recent relationship with a much younger man.
"The last guy I was dating, I met him in Vegas at a blackjack table. That was a really fun, like, adventure," she explained. "We had a great five, six months together."
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Chelsea Handler revealed her last relationship with a much younger man ended amicably.
Though the relationship reached its course, it ended amicably, and the pair remain friends.
"Maybe I’ll see him again, maybe we’ll fool around again," she joked.
Host Kristin Cavallari noted the relationship seemed serious, as Handler went "public" with him by sharing photos of them together.
Chelsea Handler Described Her Ideal Partner
Chelsea Handler confessed that she's not shy about sharing photos of her romantic conquests.
"I post guys all the time that I'm dating. I'm not posting them saying, 'This is my boyfriend.' It's like who I'm spending time with," she explained. "It's reflective of who I'm spending time with."
Handler described her ideal partner as someone she sees "like every two weeks." In addition, she said her interest varies based on their ability to go on "fun trips."
Handler ended the conversation by sharing a dating blunder with celebrity chef Bobby Flay, calling him "cheap" after he made her pay the bill when he ordered her and her friends room service.
"If you’re penurious, I’m not interested in you. I’m generous and I like people to be generous with their money," she confessed.
