Chelsea Handler Reveals ‘Bad’ Date with Bobby Flay, Calls Him ‘Cheap’: ‘It Was Not a Match’

Chelsea Handler has recently opened up about her experiences with dating in a candid appearance on Kristin Cavallari’s podcast, “Let’s Be Honest”. During the episode, Handler shared some insights into her romantic life, including a rather unfortunate date with renowned chef Bobby Flay.

The comedian recalled the ill-fated evening, explaining that she had been connected to Flay through a mutual friend. After engaging in some flirtatious conversation over the phone, she was eager to meet in person. Handler described the date as “pretty bad” and recounted a particularly awkward moment involving room service while staying at a hotel with friends.

Handler noted that Flay offered to order her food during her hotel stay. “He knew the hotel well, and he wanted to order me room service,” she stated, reflecting on the moment that soon turned embarrassing. However, when the food arrived, so did the bill, which left Handler surprised. “I’m like, what? And then somebody was like, ‘Oh, yeah, he’s really cheap.'”

The comedian went on to express her disdain for those she perceives as stingy. “If you’re penurious, I’m not interested in you,” Handler remarked. She prefers partners who are generous, particularly when it comes to finances. Despite the misstep over the meal, Handler and Flay later went on an official date, which she described as “messy” and ultimately determined that they were simply “not a match.”

In addition to her experience with Flay, Handler revealed that she had another uncomfortable date with a celebrity whose name she chose to keep private. She described the date as “unbearable,” commenting on how the individual dominated the conversation. “He couldn’t stop talking about himself, and he didn’t ask me one question about myself,” Handler recounted, feeling as though the dynamic forced her to “make up a lie” to escape the dull encounter.

She continued by expressing her frustration with the man’s seriousness about his acting career, saying, “I was like, you’re so boring, and you’re so annoying.” Handler’s desire for casual and fun interactions was apparent as she encouraged the actor to loosen up a bit during their meeting.

Handler also touched upon her current stance on relationships, confirming to Cavallari that she is no longer with her most recent boyfriend. The comedian elaborated that she is not inclined towards long-term commitments, stating, “I’m not interested in anything that comes after the six-month relationship mark.”

Rather than seeking a conventional partnership, Handler declared her preference for “a good, sexy affair.” She expressed her lack of interest in becoming part of a unit or dealing with the complexities that accompany deeper relationships. “I want to have a good, sexy affair. I don’t want to be a couple,” she asserted, solidifying her stance on modern dating.

Chelsea Handler’s frank discussion about her dating experiences and opinions on relationships provides an insightful glimpse into the life of the comedian. Her willingness to share both humorous and distressing dating anecdotes serves as a reminder that the dating scene can often be as unpredictable as it is entertaining. With her characteristic honesty and wit, Handler continues to captivate her audience, whether discussing her professional ventures or personal escapades in love.