Chelsea Handler<\/a> spilled the tea on the awkward experience she had with Bobby Flay<\/a>.<\/p>\n The comedian dished about their connection on the Tuesday, May 26, episode of Kristin Cavallari<\/a>‘s “Let’s Be Honest” podcast<\/a> when the host asked about any “bad” celebrity dates<\/a> she’s been on.<\/p>\n Chelsea Handler named Bobby Flay when asked to share a ‘bad’ date story.mega<\/p>\n<\/figcaption><\/div>\n<\/figure>\n Handler, 51, revealed someone once got her and Flay, 61, in touch, and the two started “talking on the phone [and] flirting a little bit.”<\/p>\n At the time, she was staying at a hotel with some friends, and since the chef “knew the hotel well… he was like, \u2018Let me order your food for you. I love that hotel.'”<\/p>\n However, when the food arrived, so did the check, and the comic had to pay for everything theBeat Bobby Flay<\/em> star ordered.<\/p>\n The chef ordered Chelsea Handler and her friends room service but made the comedian pay the bill.mega<\/p>\n<\/figcaption><\/div>\n<\/figure>\n “And I\u2019m like, \u2018What?’ And then somebody was like, \u2018Oh yeah. He\u2019s really cheap,\u2019” Handler recalled. “And I was like, \u2018Oh, I hate cheap.'”<\/p>\n “If you\u2019re penurious, I\u2019m not interested in you. I\u2019m generous and I like people to be generous with their money,” she explained.<\/p>\n Handler wound up giving him a second chance and the two went out in-person<\/a>, but “it was not a match. It was just like, messy,” she said.<\/p>\n Handler is currently single<\/a> but recently raved over a romance she had with a younger guy<\/a>.<\/p>\n Kristin Cavallari initially shut down Bobby Flat when he invited her to get dinner in Nashville, Tenn.lets be honest podcast\/youtube<\/p>\n<\/figcaption><\/div>\n<\/figure>\n Funny enough, Cavallari, 39, had her own experience with<\/a> the father-of-one, which they discussed when he appeared on her podcast in 2024.<\/p>\n “I DMed you and I said to you \u2026 \u2018I\u2019m going to be in Nashville for one night, can I take you to dinner?’ And you literally said something to me like, \u2018I\u2019m already dating somebody,\u2019” he recalled, to which the reality star replied, “Or I was like, \u2018I\u2019m over dating right now.\u2019 I was burnt out on dating or something.\u201d<\/p>\n The reality star admitted she assumed Bobby Flay was asking her out in a romantic way when she first declined.lets be honest podcast\/youtube<\/p>\n<\/figcaption><\/div>\n<\/figure>\n “No, you said, \u2018I\u2019ve already started seeing somebody!\u2019 And I said, \u2018I just want to go to dinner with you,\u2019\u201d he continued.<\/p>\n “It was like foot in mouth,” the mom-of-three<\/a> confessed, admitting she assumed the Food Network star meant for it to be a romantic outing. “I think the \u2018take you to dinner\u2019 thing is more where it was like, \u2018Oh, that seems like a date.'”<\/p>\n The two ended up going on a platonic dinner date, with the podcast host revealing she had “the best time.”<\/p>\n Read more at OK!<\/a><\/p>\n Get OK!’s biggest scoops and scandals delivered right to your inbox. Sign up now<\/a>.<\/p>\n FOLLOW OK! ON WHATSAPP HERE<\/a>: Stay across all the latest in celebrity, entertainment, and pop culture via our WhatsApp channel<\/a>. No comments, no algorithm and nobody can see your private details.<\/p>\n<\/div>\n \u2018 The preceding article may include information circulated by third parties \u2019 <\/em><\/p>\n \u2018 Some details of this article were extracted from the following source www.aol.com \u2019 <\/em><\/p>\n","protected":false},"excerpt":{"rendered":" Chelsea Handler spilled the tea on the awkward experience she had with Bobby Flay. The comedian dished about their connection on the Tuesday, May 26, episode of Kristin Cavallari‘s “Let’s Be Honest” podcast when the host asked about any “bad” celebrity dates she’s been on. Chelsea Handler and Bobby Flay Flirted Before They Went Out […]<\/p>\n","protected":false},"author":2,"featured_media":2432876,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"om_disable_all_campaigns":false,"_jetpack_memberships_contains_paid_content":false,"jnews-multi-image_gallery":[],"jnews_single_post":[],"jnews_primary_category":[],"jnews_social_meta":[],"footnotes":""},"categories":[25177],"tags":[351169,477334,377902,349754],"class_list":["post-2432875","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-celebrities","tag-bobby","tag-bobby-flat","tag-chelsea-handler","tag-kristin-cavallari"],"jetpack_featured_media_url":"https:\/\/celebrity.land\/en\/wp-content\/uploads\/2026\/05\/Chelsea-Handler-Drags-Cheap-Bobby-Flay-for-Being-One-of.com2Fen2Faol_ok_magazine_3022F20bfe62b1f9863ff12b9b64d6d14935f.jpeg","jetpack_sharing_enabled":true,"_links":{"self":[{"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/posts\/2432875","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/comments?post=2432875"}],"version-history":[{"count":1,"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/posts\/2432875\/revisions"}],"predecessor-version":[{"id":2432877,"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/posts\/2432875\/revisions\/2432877"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/media\/2432876"}],"wp:attachment":[{"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/media?parent=2432875"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/categories?post=2432875"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/celebrity.land\/en\/wp-json\/wp\/v2\/tags?post=2432875"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}Chelsea Handler and Bobby Flay Flirted Before They Went Out<\/h2>\n
‘It Was Not a Match’<\/h2>\n
<\/div>
Bobby Flay Once Took Kristin Cavallari Out to Dinner<\/h2>\n
<\/div>
The Pair Had ‘the Best Time’<\/h2>\n
<\/div>