Old School. Biblically Independent.
By Dustin Rowles | Celebrity | November 19, 2025
Yesterday, we learned from journalist Olivia Nuzzi’s ex-fiancé, Ryan Lizza, that before Nuzzi had an affair with a 2024 presidential candidate, she also had an affair with a 2020 presidential candidate. But Nuzzi’s pattern of dating men more than 30 years her senior didn’t begin with Mark Sanford or Robert F. Kennedy Jr. As Lizza noted in his write-up, before he and Nuzzi began dating, he helped her extricate herself from a four-year relationship with Keith Olbermann.
I didn’t think too much of that at the time, because Nuzzi’s relationship with Olbermann wasn’t a secret. In fact, last year, when the story broke that Nuzzi and RFK Jr. had an affair, Olbermann admitted on his podcast that he had a romantic history with Nuzzi, saying they dated for three years when he was 55 and she was 21. At the time, I wrote that Olbermann didn’t offer many details about their relationship, except to say that her parents weren’t the best role models, “which sounds like something a man more than twice his girlfriend’s age might say.”
A 55-year-old man dating a 21-year-old college student is not good. But what I didn’t consider then was that the three-year relationship ended when she was 21, which means … well, Sarah Lyons over on the House of Mirrors Substack did the math yesterday.
Olbermann has not refuted this relationship, and claims it lasted for about 4 years. So, if what has been alleged is true, and Olbermann supposedly began dating Nuzzi out of high school when she “fled her unhappy home” and “he paid for her to attend college”, that would put their relationship between 2011-2015. Again, this is me reading between the lines of available information. If correct, at 34 years her senior, Olbermann would have started dating Nuzzi when she was 18 and he was 52.
Umm. Why was Olbermann dating someone right out of high school? How did he even meet someone right out of high school? And I don’t think this is the winning hand Olbermann thinks it is:
As Sarah Lyons noted, this was also around the time Nuzzi took a shot at being a pop star. Here’s her MySpace page from then.
Nor is the joke about Olbermann dodging a bullet particularly charming.
I should also note that although Olbermann said last year that he dated her for three years, he conceded yesterday that it was four. Are we even sure she was 18 at the time? And has Olbermann chimed in on Megyn Kelly’s latest comments? Oh, he has.
That aged poorly in only five days. It’s a good thing Olbermann doesn’t have much of a career left to lose.
