In her memoir “Going There,” Katie Couric opened up about a fling that she had with playwright Neil Simon in 1985. She was 28 years old at the time and Simon was 30 years her senior. That didn’t seem to bother the rising television star at the time, as she wrote that being “in the presence of such an icon was thrilling,” and that she was willing to do whatever it took to “get him to notice” her, which included wearing a white dress and putting on her favorite shade of Max Factor lipstick, per Page Six.
“I was completely, utterly, and crazily starstruck,” Couric wrote, adding that her plan must have worked because she noticed that Simon was checking her out. Things seemed to heat up between them as by their second date Simon invited Couric up to his hotel room, where they began kissing passionately. Yet, their night ended when her date supposedly told Couric three very important words. And no, it’s not the three words she was expecting. Simon ended their make-out session when he suddenly remembered that he had to take his “blood pressure medication” recalls Couric.
Things didn’t work out the way Couric hoped, but she did confess that the entire encounter was “strange, being with someone 30 years older… but I was all for new experiences.”