Chelsea Handler has been there, done that, and she is back!

The Hollywood personality just declared that things have come to an end between her and her former boyfriend, Joe Largura, a few months after they became public, and the dating scene has not been impressive for the media personality.

Chelsea Handler has enjoyed quite a roster of high-profile relationships, including one with rapper and businessman 50 Cent and comedian Jo Koy from 2021 to 2022. 

Chelsea Handler Insists She Is Cordial With Joe Largura

The media personality opened up about her relationship with the mystery man during a recent appearance on “Let’s Be Honest with Kristin Cavallari” podcast.

The private relationship with the guy whom she nicknamed “cowboy” lasted around five to six months after their meet-cute at a blackjack table in Las Vegas.

As stated by the comedian, her brief romance with Largura was exciting and enjoyable, but things ran their natural course between them.

Largura has appeared alongside Handler on vacations in Turkey, Finland, Jamaica, and Canada, raising eyebrows about the seriousness of the relationship.

The media personality continued that her typical timeframe for a relationship lasts for about six months before the novelty fades for her.

Despite this, Handler confirmed that they separated amicably and there is a chance they could rekindle things casually in the future.

The star continued on the podcast that she does not see herself wanting the responsibilities that often come with long-term relationships, including handling family dynamics or becoming part of a tightly connected couple unit. Instead, the media personality enjoys passionate, fun relationships without the expectations of permanence.

The Former E! Star Slammed Modern Dating Culture For Leaving Women Frustrated

Handler also got candid about the way people date these days, saying she feels that today’s dating culture has made it harder to find any worthwhile relationship.

On the “Howie Mandel Does Stuff” podcast, Handler talked about her own personal experiences in the realm of romance, as well as her friends’ experiences.

The comedian stated that dating apps and social media have revolutionized the dynamics of relationships, particularly in the context of dating a woman.

As stated by The Blast, she added that the “bazaar” of choices online has made people less willing to commit to one person fully.

She opined that many men are no longer under pressure to invest heavily in relationships because dating apps make them believe there is always someone else who is just a swipe away.

Handler also complained about the lack of emotionally mature and stable men she has seen in the dating scene in recent years, and she admitted she still has no idea how so many relationships die an early death.

The actress continued that she started to notice more of the situation while trying to match her female friends with a man.

She emphasized that modern dating sites seem to promote platonic relationships more than permanent ones, which will make it tough for folks to dedicate the time that was traditionally needed in relationships.

“I meet all these amazing, incredible women that are like bad-ss. They have their own lives. They have their big jobs, and they’re all just like, “There’s no men out there,” Handler concluded.

Chelsea Handler Values Her Independence Over Any Other Arrangement 

Despite recently criticizing modern dating culture, Chelsea Handler says she still enjoys dating, just without the pressure of serious commitment.

The comedian and television personality said she is still out and about and is looking for new friendships, but for now, she is not interested in settling on anything.

Rather than describing herself as being in a committed relationship, Handler shared that she is simply exploring different experiences and enjoying various aspects of her personal life. 

She also pointed out that independence is very much a part of her life and that she does not want to feel confined, emotionally attached, or restricted by one person.

Throughout the years, Handler has been vocal about putting freedom, self-growth, and personal happiness over traditional relationship expectations like marriage or long-term relationships.

In a recent interview with the “Angie Martinez IRL” podcast in April 2026, Handler also discussed her passion for life on her own terms. One of the things the comedian loves about being single is that she doesn’t have to seek advice from anyone to make decisions. 

From booking a spontaneous trip to rearranging plans on the spur of the moment, Handler admits that she appreciates the freedom to do what she wants without having to ask permission from a partner or compromise.

The ‘Chelsea Lately’ Star Admitted How She Made Dating In Her 50s Fun

The Blast noted that during a March appearance on “The View,” Handler opened up about her relationship with Largura and revealed why she recently decided to start dating younger men.

Following the hosts’ mention of a “hard launch” of her romance on social media, Handler clarified that she was “subtly introducing a romance without making any ‘love statements’ or officially announcing him as her boyfriend.

Handler also revealed that her present relationship has already been longer than some of her past relationships. She shared that her partner is 37 years old, and after dating older men for years, she decided to challenge herself and date younger men after the age of 50.

The two reportedly hit it off at a blackjack table at The Cosmopolitan in Las Vegas during a November 2025 meeting. One of their encounters was a random request for a $1,000 loan in an attempt by Handler to get some money from him when he was on a winning streak.

Why Chelsea Handler Had To Call Things Off With Jo Koy

In her review of her dalliance with comedian Jo Koy, Handler shared that the experience really altered her perspective on love and emotional connection.

According to her, the relationship gave her a renewed sense of trust in men, love, and living her life to the fullest. However, as their friendship grew, she eventually realized that they were not always meant to be.

The comedian continued that their differences grew so big that they could not ignore them, and that it would have meant that she would have had to give up parts of herself to stay in the relationship.

The split came up again in a December 2022 podcast segment with Brooke Shields, when she admitted that she previously thought Koy might have been her lifetime partner and even considered marrying him.

Handler noted that the split would have involved too much compromise, as there were unresolved behavioral differences and persistent arguments between them.

She emphasized that she might have sacrificed a piece of herself in a relationship when she was younger, but now she was not willing to do that, even if the person she loved was a good person.

Chelsea Handler seems to be having the time of her life in her new era!