Chelsea Handler name-drops ‘cheap’ A-list chef who took her on ‘bad’ date

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Worst date in America?

Chelsea Handler recalled a ā€œbadā€ dating experience she had with celebrity chef Bobby Flay.

During an appearance on Kristin Cavallari’s ā€œLet’s Be Honestā€ podcast Tuesday, the former reality star asked the comedian to share a ā€œbad celebrity date storyā€ that she hasn’t told before.

ā€œYeah, I went on a date with Bobby Flay. That was pretty bad,ā€ Handler, 51, claimed.

ā€œHe ordered me room service. So, we were talking — someone hooked us up — we were talking on the phone, flirting a little bit,ā€ the ā€œChelsea Latelyā€ alum added.

ā€œI was at a hotel with some girlfriends … he knew the hotel well. He wanted to order me room service, food for us. He’s like, ā€˜Let me order your food for you. I love that hotel.ā€™ā€

Handler said Flay, 61, ordered their food but the hotel ended up bringing her the bill.

ā€œAnd I’m like, ā€˜What?’ And then somebody was like, ā€˜Oh yeah. He’s really cheap.’ And I was like, ā€˜Oh, I hate cheap,ā€™ā€ she recalled.

ā€œIf you’re penurious, I’m not interested in you. I’m generous and I like people to be generous with their money,ā€ Handler shared.

Despite the food service blunder, Handler said she later went on a date with the ā€œBeat Bobby Flayā€ star.

ā€œThen we did end up going on a date … it was not a match,ā€ she said, adding, ā€œIt was just like, messy.ā€

Page Six has reached out to Flay’s rep for comment but did not immediately hear back.

In November 2024, Flay revealed on Cavallari’s podcast that she rejected his flirty messages.

ā€œI DMed you and I said to you … ā€˜I’m going to be in Nashville for one night. Can I take you to dinner?ā€™ā€ he said at the time.

ā€œAnd you literally said something to me like, ā€˜I’m already dating somebody,ā€™ā€ Flay recalled.

The ā€œHilsā€ alum, 39, claimed she actually responded by saying that she was ā€œburnt outā€ with dating — but Flay doubled down.

ā€œNo, you said, ā€˜I’ve already started seeing somebody!’ And I said, ā€˜I just want to go to dinner with you,ā€™ā€ he replied with a laugh, explaining that he just wanted to meet up as friends.

The cookbook author is currently in a relationship with fellow chef Brooke Williamson.

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