{"id":823391,"date":"2026-05-26T14:07:21","date_gmt":"2026-05-26T14:07:21","guid":{"rendered":"https:\/\/www.europesays.com\/us\/823391\/"},"modified":"2026-05-26T14:07:21","modified_gmt":"2026-05-26T14:07:21","slug":"chelsea-handler-name-drops-cheap-a-list-chef-who-took-her-on-bad-date","status":"publish","type":"post","link":"https:\/\/www.europesays.com\/us\/823391\/","title":{"rendered":"Chelsea Handler name-drops &#8216;cheap&#8217; A-list chef who took her on &#8216;bad&#8217; date"},"content":{"rendered":"<p>Worst date in America?<\/p>\n<p>Chelsea Handler spilled the tea on her \u201cbad\u201d dating experience with celebrity chef Bobby Flay during Kristin Cavallari\u2019s <a href=\"https:\/\/open.spotify.com\/episode\/5WpEy5NKGCNHxi5AfGDJON\" target=\"_blank\" rel=\"noopener nofollow\">\u201cLet\u2019s Be Honest\u201d podcast<\/a> Tuesday.<\/p>\n<p>When the host asked Handler, 51, to share a \u201cbad celebrity date story\u201d that she hasn\u2019t told before, the comedian immediately named Flay.<\/p>\n<p>Chelsea Handler (seen waving in 2024) recalled a \u201cbad\u201d dating experience she had with Bobby Flay.  GC Images<\/p>\n<p>The comedian said the chef (seen above holding a plate of food) offered to purchase hotel room service for her and her friends. ABC via Getty Images<\/p>\n<p>After \u201csomeone hooked [them] up,\u201d the duo \u201cwere talking on the phone [and] flirting a little bit,\u201d which led to Flay ordering Handler room service.<\/p>\n<p>\u201cI was at a hotel with some girlfriends,\u201d the \u201cChelsea Lately\u201d alum recalled. \u201cHe knew the hotel well. He wanted to order \u2026 food for us. He was like, \u2018Let me order your food for you. I love that hotel.&#8217;\u201d<\/p>\n<p>Handler claimed Flay, 61, ordered the food \u2014 but the hotel brought her the bill.<\/p>\n<p>\u201cAnd I\u2019m like, \u2018What?&#8217;\u201d she remembered thinking. \u201cAnd then somebody was like, \u2018Oh yeah. He\u2019s really cheap.\u2019 And I was like, \u2018Oh, I hate cheap.&#8217;\u201d<\/p>\n<p>Handler (seen above in a selfie) said she was shocked to be left with the bill. chelseahandler\/Instagram<\/p>\n<p>The former talk show host (seen at the Kevin Hart roast in May) said someone told her Flay was \u201creally cheap.\u201d Getty Images for Netflix<\/p>\n<p>\t\t\t\t\t\t\tWant more celebrity and pop culture news?\t\t\t\t\t\t<\/p>\n<p class=\"inline-module__cta\">\n\t\t\t\t\t\t\tStart your day with Page Six Daily.\t\t\t\t\t\t<\/p>\n<p>\t\t\t\t\t\tThanks for signing up!\n\t\t\t\t<\/p>\n<p>\u201cIf you\u2019re penurious, I\u2019m not interested in you. I\u2019m generous and I like people to be generous with their money,\u201d Handler shared.<\/p>\n<p>Despite the food service blunder, Handler later went on a date with the \u201cBeat Bobby Flay\u201d star, but \u201cit was not a match.\u201d<\/p>\n<p>Handler did not elaborate further, simply saying, \u201cIt was just like, messy.\u201d<\/p>\n<p>Page Six has reached out to Flay\u2019s rep for comment but did not immediately hear back.<\/p>\n<p>Handler (seen above at BottleRock Napa Valley in May) said she later went on a date with the cookbook author but claimed it was \u201cmessy.\u201d AP Photo\/Amy Harris<\/p>\n<p>In 2024, Flay (seen in NYC in May) claimed Kristin Cavallari rejected his flirty DM. GC Images<\/p>\n<p>In November 2024, Flay revealed on Cavallari\u2019s podcast that she once <a href=\"https:\/\/pagesix.com\/2024\/10\/29\/celebrity-news\/kristin-cavallari-admits-she-shot-down-bobby-flay-when-he-slid-into-her-dms\/\" rel=\"nofollow noopener\" target=\"_blank\">rejected his flirty messages<\/a>.<\/p>\n<p>\u201cI DMed you and I said to you \u2026 \u2018I\u2019m going to be in Nashville for one night. Can I take you to dinner?\u2019\u201d he said at the time.<\/p>\n<p>\u201cAnd you literally said something to me like, \u2018I\u2019m already dating somebody,\u2019\u201d Flay recalled.<\/p>\n<p>The restaurateur (seen above at the 2026 South Beach Wine &amp; Food Festival) clarified that he just wanted to take the \u201cHills\u201d alum to dinner \u201cas friends.\u201d Getty Images<\/p>\n<p>Flay is currently dating chef Brooke Williamson (seen above). GC Images<\/p>\n<p>The \u201cHills\u201d alum, 39, claimed she actually responded by saying she was \u201cburnt out\u201d with dating \u2014 but Flay doubled down.<\/p>\n<p>\u201cNo, you said, \u2018I\u2019ve already started seeing somebody!\u2019 And I said, \u2018I just want to go to dinner with you,\u2019\u201d he replied with a laugh, explaining that he just wanted to meet up as friends.<\/p>\n<p>The cookbook author is currently in a relationship with <a href=\"https:\/\/pagesix.com\/celebrity-news\/who-is-brooke-williamson-meet-bobby-flays-new-girlfriend\/\" rel=\"nofollow noopener\" target=\"_blank\">fellow chef Brooke Williamson<\/a>.<\/p>\n","protected":false},"excerpt":{"rendered":"Worst date in America? Chelsea Handler spilled the tea on her \u201cbad\u201d dating experience with celebrity chef Bobby&hellip;\n","protected":false},"author":3,"featured_media":823392,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":"","_share_on_mastodon":"0"},"categories":[33],"tags":[116636,185,338399,91039,4349,571,174,172,222165,7882,171,5158,173,67,132,68],"class_list":["post-823391","post","type-post","status-publish","format-standard","has-post-thumbnail","category-celebrities","tag-bobby-flay","tag-celebrities","tag-celebrity-cheapskates","tag-celebrity-chefs","tag-celebrity-dating","tag-celebrity-exes","tag-celebrity-interviews","tag-celebrity-news","tag-chelsea-handler","tag-comedians","tag-entertainment","tag-podcasts","tag-tv","tag-united-states","tag-unitedstates","tag-us"],"share_on_mastodon":{"url":"https:\/\/pubeurope.com\/@us\/116641270865945552","error":""},"_links":{"self":[{"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/posts\/823391","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/users\/3"}],"replies":[{"embeddable":true,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/comments?post=823391"}],"version-history":[{"count":0,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/posts\/823391\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/media\/823392"}],"wp:attachment":[{"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/media?parent=823391"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/categories?post=823391"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.europesays.com\/us\/wp-json\/wp\/v2\/tags?post=823391"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}