Chelsea Handler Recalls Going on ‘Bad’ Date With Food Network’s Bobby Flay

According to Handler, she and Flay met through mutual friends and flirted over the phone “for a little bit” before meeting in person. I was at a hotel with some girlfriends, and I think we were filming for Netflix,” she shared. “He knew the hotel well, and he’s like — oh, my god. He wanted to order me room service, food for us. He was like, ‘Let me order your food for you. I love that hotel.'”

Before continuing her story, she stopped to joke, “This is somebody I don’t mind incriminating.” Handler went on to share, “Three of my girlfriends are in the room with me, and they ordered room service. He’s like, ‘I’m going to order it.’ But then, they brought me the bill. And I’m like, ‘What? Is this guy…’ And then, somebody was like, ‘Oh yeah, he’s really cheap. He’s really cheap.’ And I was like, ‘Oh, I hate cheap.'”

She noted, “If you’re penurious, I’m not interested in you. I’m generous, and I like people to be generous with their money.”

Despite the alleged incident, Handler said she and Flay still went on a date. However, “it was not a match,” she stated. “It was just, like, it was messy.” (Flay has not publicly reacted to Handler’s dating story.)

Handler has been romantically connected to several famous names over the years, including 50 Cent and Jo Koy. Flay, meanwhile, was previously married three times and has been dating his fellow Food Network star, Brooke Williamson, since last year.

Handler shared another not-so-great dating story on Cavallari’s podcast, though she didn’t reveal her celebrity date’s name.

“I made the move. I was like, ‘Hey, I want to get in on this.’ And so, I made the move, and he was receptive, and we were hanging out,” she said. “And I saw him, and we went on a date, and it was unbearable. Unbearable. And I worked hard. He was so serious about himself as an actor, and he was talking about acting in a way that I cannot take seriously. Like, I’m not like that. I’m not an actor. I am an entertainer. Okay? And I just couldn’t believe how solipsistic this guy was. He couldn’t stop talking about himself.”

Though her date didn’t ask her “one question” about herself, Handler said the actor thought the night “went great.” She joked, “I felt like I was 25 years old and had to like make up a lie to get away because I had really pursued him. But once I sat down with him, I was like, ‘No, no.’ I was like, ‘You’re so boring, and you’re so annoying.’ Anyone who talks about themselves for that long on a date is just, that’s exactly what’s wrong with men.”

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