{"id":3545,"date":"2026-05-26T17:27:27","date_gmt":"2026-05-26T17:27:27","guid":{"rendered":"https:\/\/login9ja.com\/global\/chelsea-handler-eviscerates-serious-actor-she-went-on-unbearable-date-with-teases-nice-little-affair-with-a-lister\/"},"modified":"2026-05-26T17:27:27","modified_gmt":"2026-05-26T17:27:27","slug":"chelsea-handler-eviscerates-serious-actor-she-went-on-unbearable-date-with-teases-nice-little-affair-with-a-lister","status":"publish","type":"post","link":"https:\/\/login9ja.com\/global\/chelsea-handler-eviscerates-serious-actor-she-went-on-unbearable-date-with-teases-nice-little-affair-with-a-lister\/","title":{"rendered":"Chelsea Handler eviscerates &#8216;serious&#8217; actor she went on &#8216;unbearable&#8217; date with, teases &#8216;nice little affair&#8217; with A-lister"},"content":{"rendered":"<p><img decoding=\"async\" src=\"https:\/\/pagesix.com\/wp-content%2Fuploads%2Fsites%2F3%2F2026%2F05%2F128764151.jpg?quality%3D90%26strip%3Dall\" \/><\/p>\n<div>\n<p>Chelsea Handler\u2019s horizontal life includes a few secret A-listers. <\/p>\n<p>The comedian got candid about an \u201cunbearable\u201d date she once went on with an unnamed celebrity.<\/p>\n<p>\u201cHe was so boring. But I can\u2019t tell you the name. I just can\u2019t,\u201d Handler, 51, teased while on Tuesday\u2019s episode of Kristin Cavallari\u2019s\u00a0<a href=\"https:\/\/open.spotify.com\/episode\/5WpEy5NKGCNHxi5AfGDJON\" target=\"_blank\" rel=\"noreferrer noopener\">\u201cLet\u2019s Be Honest\u201d podcast<\/a>.<\/p>\n<p>The stand-up explained that she made the first move, but her mystery man was \u201creceptive.\u201d<\/p>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-full\"><figcaption>Chelsea Handler (pictured here on Kristin Cavallari\u2019s podcast on Tuesday) opened up about an \u201cunbearable\u201d date she went on with an unnamed celebrity.  <span class=\"credit\">YouTube\/Let&#8217;s Be Honest with Kristin Cavallari<\/span><\/figcaption><\/figure>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-full\"><figcaption>The comedian called the actor \u201cso boring,\u201d and claimed he only spoke about himself and his acting process. <span class=\"credit\">YouTube\/Let&#8217;s Be Honest with Kristin Cavallari<\/span><\/figcaption><\/figure>\n<aside class=\"single__inline-module aligncenter wp-block-nypost-editor-primary-tag\">\n<\/aside>\n<p>\u201cWe went on a date and it was unbearable. And I worked hard,\u201d Handler confessed. \u201cHe was so serious about himself as an actor.\u201d<\/p>\n<p>Calling her courter \u201cso boring,\u201d the author added that \u201che was talking about acting in a way I can\u2019t take seriously.\u201d<\/p>\n<p>Not being an actress herself, but an \u201centertainer,\u201d Handler couldn\u2019t believe how self-obsessed her date was.<\/p>\n<p>\u201cHe didn\u2019t ask me one question about myself,\u201d she recounted. \u201cI was like, \u2018Oh, okay.&#8217;\u201d <\/p>\n<p>However, the pair had a different version of events \u2014 with the actor thinking the night went \u201cgreat.\u201d<\/p>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-full\"><figcaption>The stand-up recalled, \u201cHe didn\u2019t ask me one question about myself. I was like, \u2018Oh, okay.&#8217;\u201d  <span class=\"credit\">YouTube\/Let&#8217;s Be Honest with Kristin Cavallari<\/span><\/figcaption><\/figure>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-full\"><figcaption>The author said her mystery man felt the date went great and she had to make up an excuse to jump ship. <span class=\"credit\">YouTube\/Let&#8217;s Be Honest with Kristin Cavallari<\/span><\/figcaption><\/figure>\n<p>Handler and her potential suitor, meanwhile, met in America but went out together in a different country.<\/p>\n<p>\u201cI had really gone out of my way. I was on my way somewhere and I stopped for the night in a city to go on a date with this guy,\u201d the \u201cChelsea Lately\u201d alum admitted. <\/p>\n<p>Handler said she felt like a woman in her 20s who had to come up with a lie to escape the disastrous evening.<\/p>\n<p>\u201cI had really pursued him, but once I sat down with him, I was like, \u2018You\u2019re so boring and so annoying.&#8217;\u201d<\/p>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-full\"><figcaption>The former talk show host (pictured here in May) also recounted one \u201cnice little affair\u201d she had with a fellow A-lister. <span class=\"credit\">Xavier Collin\/Image Press Agency \/ BACKGRID<\/span><\/figcaption><\/figure>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-full\"><figcaption>The actress (pictured here in January) added that her dalliance only lasted a few months. <span class=\"credit\">Getty Images<\/span><\/figcaption><\/figure>\n<p><a href=\"https:\/\/pagesix.com\/2026\/05\/14\/celebrity-news\/chelsea-handler-slams-modern-dating-culture-says-men-struggle-to-commit\/\">\u201cThat\u2019s what\u2019s wrong with men,\u201d Handler stated<\/a>. \u201cHe was very much about himself, and his process and his acting.\u201d<\/p>\n<p>The comic was hoping the two could take the conversation to a lighter place, but the moment never arose. <\/p>\n<p>Meanwhile, without naming names \u2014 for a second time \u2014 Handler also told Cavallari, 39, she had \u201ca nice little affair\u201d with one major celeb. <\/p>\n<p>\u201cThat wasn\u2019t even long term. It was a few months,\u201d she continued. <\/p>\n<p>However, Handler didn\u2019t shy away from dropping one known moniker. <\/p>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-full\"><figcaption>During her interview, Handler also called her dated with chef Bobby Flay (pictured here in May) \u201cbad,\u201d and claimed he stuck her with the bill. <span class=\"credit\">ABC via Getty Images<\/span><\/figcaption><\/figure>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-full\"><figcaption>The television personality was previously linked to Jo Koy (pictured here together in 2022) for less than a year before their 2022 split. <span class=\"credit\">Penske Media via Getty Images<\/span><\/figcaption><\/figure>\n<p>She called her<a href=\"https:\/\/pagesix.com\/2026\/05\/26\/celebrity-news\/chelsea-handler-name-drops-cheap-a-list-chef-who-took-her-on-bad-date\/\"> night out with Bobby Flay<\/a>: \u201cJust bad.\u201d<\/p>\n<p>Handler claimed that the chef, 61, ordered room service but stuck <em>her<\/em> with the bill.<\/p>\n<p>The duo tried going out once more, but according to Handler, \u201cIt was just like, messy.\u201d<\/p>\n<p>Handler\u2019s confessions come a few years after\u00a0<a href=\"https:\/\/pagesix.com\/2025\/02\/10\/celebrity-news\/chelsea-handler-had-no-choice-but-to-break-up-with-jo-koy-over-his-old-fashioned-expectations\/\">her\u00a0breakup from fellow comedian Jo\u00a0Koy<\/a>.<\/p>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-full\"><figcaption>The comic also dated businessman Andre Balazs (pictured here together in 2013) from 2011 until 2013.  <span class=\"credit\">Donato Sardella<\/span><\/figcaption><\/figure>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-full\"><figcaption>Along with 50 Cent and Animal Planet star, Dave Salmoni, Handler also dated Comcast CEO Ted Harbert (pictured here together in 2008) for four years in the mid-2000s. <span class=\"credit\">Patrick McMullan via Getty Images<\/span><\/figcaption><\/figure>\n<p>The former flames dated for less than a year before calling it quits in 2022.<\/p>\n<p><a href=\"https:\/\/pagesix.com\/celebrity-news\/chelsea-handler-dating-history\/\">Handler previously dated Comcast CEO Ted Harbert<\/a> for four years from 2006 until 2010. <\/p>\n<p>That same year, she struck up a romance with Animal Planet star Dave Salmoni. <\/p>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-full\"><figcaption>The producer recently debuted her new romance in March (as pictured here in an Instagram photo). <span class=\"credit\">chelseahandler\/Instagram<\/span><\/figcaption><\/figure>\n<figure class=\"nyp-slideshow-modal-image wp-block-image aligncenter size-full\"><figcaption>The \u201cMy Horizontal Life\u201d author (pictured here with her new beau) only refers to her partner as \u201cCowboy.\u201d  <span class=\"credit\">chelseahandler\/Instagram<\/span><\/figcaption><\/figure>\n<p>Handler was also briefly linked to  50 Cent, whom she\u2019s dubbed her \u201cfavorite ex,\u201d in 2011.<\/p>\n<p>The talk show host and businessman Andre Balazs\u00a0<a href=\"https:\/\/pagesix.com\/2013\/03\/12\/chelsea-handler-gushes-over-her-match-andre-balzas\/\">were romantically linked between 2011 and 2013<\/a>.<\/p>\n<p>In March, Handler debuted her new romance with a mystery man she <a href=\"https:\/\/www.instagram.com\/p\/DVq2-HEjee3\/?hl=en&amp;img_index=2\" target=\"_blank\" rel=\"noopener\">calls \u201cCowboy,\u201d on Instagram<\/a>.<\/p>\n<p>The carousel included pictures from the couple\u2019s trip to Istanbul in Turkey. <\/p>\n<\/p><\/div>\n<p><script async src=\"\/\/www.instagram.com\/embed.js\"><\/script><\/p>\n<p><a href=\"https:\/\/pagesix.com\/2026\/05\/26\/celebrity-news\/chelsea-handler-eviscerates-serious-actor-she-went-on-unbearable-date-with-teases-nice-little-affair-with-a-lister\/\" target=\"_blank\">Source link<\/a><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Chelsea Handler\u2019s horizontal life includes a few secret A-listers. The comedian got candid about an<\/p>\n","protected":false},"author":1,"featured_media":3546,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"_jetpack_memberships_contains_paid_content":false,"footnotes":""},"categories":[3],"tags":[],"class_list":["post-3545","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-entertainment"],"jetpack_featured_media_url":"https:\/\/login9ja.com\/global\/wp-content\/uploads\/2026\/05\/128764151.jpg","jetpack_sharing_enabled":true,"_links":{"self":[{"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/posts\/3545","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/comments?post=3545"}],"version-history":[{"count":0,"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/posts\/3545\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/media\/3546"}],"wp:attachment":[{"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/media?parent=3545"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/categories?post=3545"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/login9ja.com\/global\/wp-json\/wp\/v2\/tags?post=3545"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}