“We made small talk,” Dean wrote in Mostly Sunny. “He asked how I was and said I looked nice and that he wanted to get to know me a little better. After our wine was brought to the table, he reached over and grabbed my hand. And held it. Like a date. Did I have a boyfriend? … Was it serious? He was still holding my hand awkwardly across the table and asked if I had thought about him after our last meeting.”
The meeting left Dean “bewildered,” she wrote. She later shared the story with her therapist, her now-husband and several of her friends, including her former colleague Megyn Kelly. “We shared our Roger Ailes stories years before the Gretchen Carlson lawsuit,” she wrote of the July 2016 legal action that ended Ailes’ tenure at Fox News.
Things got worse when Ailes called to offer Dean a job. “So, how are you at phone sex?” he asked her. “WHAT!? Did I hear him right?” she wrote. “Did he ask me how I was at phone sex? My comedic instinct kicked in and I treated it like a joke. ‘I’M TERRIBLE!'” Ailes responded, “Really? You don’t seem like you’d be terrible. You’re a little naughty. I see that side of you. You’ve played phone sex with your boyfriends before, right? Let me hear what you’d say to him … like if I was your boyfriend.”