Chelsea Handler is embracing the single life once again after an exciting romance with a dashing “cowboy” she encountered at a Las Vegas blackjack table. The 51-year-old comedian recently opened up about this whirlwind international romance on the “Let’s Be Honest with Kristin Cavallari” podcast.
During her chat with 39-year-old Cavallari, Handler shared insights into her six-month relationship with the enigmatic man she affectionately calls a “cowboy.” Despite the relationship’s end, she emphasized that there were no hard feelings between them.
“The last guy I was dating, I met him in Vegas at a blackjack table. That was a really fun adventure,” Handler recounted. “We had a great five, six months together.” Their time together was indeed adventurous, as they traveled to destinations like Turkey, Finland, Jamaica, and Canada, with many of these trips documented on Handler’s Instagram earlier this year.
Handler also revealed that her relationships tend to follow a pattern, often wrapping up around the six-month mark when the initial excitement begins to fade. For her, this timeline seems to be the natural point to move on.
Earlier this year, the handsome mystery man made multiple appearances on her Instagram as they vacationed in Turkey, Finland, Jamaica and Canada together.
Handler admitted that she usually feels ready to move on from a relationship after six months as it fits her ‘timeline’ until the initial ‘buzz’ wears off.
Chelsea Handler has revealed she is single and ready to mingle after a whirlwind worldwide relationship with a handsome ‘cowboy’ whom she met at a blackjack table in Las Vegas
The comedian explained that she and her ex remain amicable and since it was a casual romance a friendship remains possible.
She explained: ‘Maybe I’ll see him again, maybe we’ll fool around again.’
Handler also said that even if ‘cowboy’ had been all over her social media, it was not ever intended to show that it was serious between them.
She said: ‘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.’
Despite posting her former beau on social media, Handler has been private about her romantic life in recent years as last year she was linked to Oscar nominated actor Ralph Fiennes.
Handler is said to have previously romanced comedian Jo Koy, chef Bobby Flay, hotelier André Balazs, rapper 50 Cent, comedian David Alan Grier, and former Comcast Entertainment Group CEO Ted Harbert.
The comedian said that she is not interested in a committed, long-term partnership at this point in her life and opts for more uncomplicated relationships.
The 51-year-old comedian talked about her most recent relationship which she documented on social media in recent months
Handler was open during an appearance on the Let’s Be Honest with Kristin Cavallari podcast
Handler revealed that her relationship with the mystery man – whom she refers to a ‘cowboy’ – ended roughly after six months with no hard feelings between them
She told 39-year-old Cavallari: ‘The last guy I was dating, I met him in Vegas at a blackjack table. That was a really fun, like, adventure. We had a great five, six months together’
Earlier this year, the handsome mystery man made multiple appearances on her Instagram as they vacationed in Turkey, Finland , Jamaica and Canada together
In March, Handler famously posted this nude photo from the snow while on vacation in Finland with ‘cowboy’
She said: ‘I am not a long-term person. I’m not interested in anything that comes after the six-month relationship mark. I’m not interested in dealing with your family or your issues. I am not interested.
‘I don’t want to be part of a unit. I want to have a good, sexy affair. I don’t want to be a couple.’
Meanwhile, the star recently said ‘something’s wrong’ with men while lamenting about the pitfalls of modern dating culture.
Handler shared a candid confession about her own experience with dating as well as what she has noticed about modern romance nowadays.
She criticized dating apps for taking away from romance and commitment, which she said she noticed particularly in heterosexual relationships.
‘It’s very hard in today’s world to meet straight guys that have their s*** together,’ she complained during an appearance on the Howie Mandel Does Stuff podcast.
‘Something’s wrong. I don’t know what’s wrong,’ continued the actress — who was especially targeted in a savage roast earlier this week.
The television host – who has dated 50 Cent, André Balazs and Jo Koy – explained that she noticed the negative aspects of modern dating culture when she was trying to help set up her friends.
Meanwhile, the star recently said ‘something’s wrong’ with men while lamenting about the pitfalls of modern dating culture
The comedian opened up about her experience with dating as well as what she has noticed about modern romance for other people nowadays
‘I was initially trying to help straight women meet straight men,’ she said.
‘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,’ she continued.
She also said dating apps are not always conducive to commitment and works better for casual relationships.
‘They can swipe through 50 women a day,’ Handler said. ‘So they’re not making the effort that people used to make to date.’
She claimed that the single women she knows have no shortage of great qualities but continuously run into the same dead end.
‘I meet all these amazing, incredible women that are like bada**,’ she said.
‘They have their own lives. They have their big jobs and they’re all just like, “There’s no men out there.”‘
