Keith Olbermann’s Dating History Resurfaces After Ryan Lizza’s Allegations

After Olivia Nuzzi’s former fiancé, Ryan Lizza, dropped a bombshell Substack about her alleged relationship with former South Carolina Gov. Mark Sanford while she was covering him, Keith Olbermann jumped on X to clown the situation. He reposted a Matrix GIF of Neo dodging bullets and implied he’d escaped a mess by not being with her anymore.

Ryan also painted Keith as a wealthy, controlling older boyfriend who paid for Olivia’s college, rent, and designer wardrobe. Keith clapped back and said they lived together for “4+ years.” He downplayed the gifts and joked, “What was I supposed to do? Get her gift certificates from Kmart?” The exchange has reignited interest in Keith’s dating history, and netizens are racing to learn more about his love life. Here’s what we know.

Keith’s relationship with Olivia is at the center of the current drama. According to the New York Post, Keith confirmed that he dated Olivia about a decade ago, when he was 55 and she was around 21. He says they haven’t spoken in roughly 10 years. At the time, she was a young political writer finishing school and breaking into national media. However, Keith did not share more details with The Post. “I keep my personal relationships close to the vest,” he said.

Before Olivia, Keith’s most-discussed relationship was with MSNBC anchor Katy Tur. Katy met Keith in the mid-2000s while she was still building her TV career. After college, she landed a temporary newsroom job that led to a meeting with the Countdown host, OK! Magazine reports. She soon moved to New York and into his apartment. The two dated from about 2006 to 2009. In her memoir Rough Draft, Tur writes that once the media realized Keith was living with a 23-year-old reporter, the relationship began to fall apart.

Olbermann added an elected official to his dating history when he revealed in 2022 that he once dated Arizona Sen. Kyrsten Sinema. On X, he said their relationship took place when she was an Arizona state legislator, writing, “When we dated, in 2010 to 11, Kyrsten was a legit progressive, far to my left.” He went public with that history while blasting Sinema for cozying up to Senate Republican leader Mitch McConnell and defending the filibuster.

However, one of the more surprising couplings in Olbermann’s relationship history is his brief fling with conservative Fox News host Laura Ingraham. According to the New York Post, the pair dated in 1997, long before Ingraham became a primetime Fox personality and before he fully shifted into hard-edged political commentary himself. The two now sit on opposite ends of the cable-news spectrum, and there’s no sign they’ve stayed close.

Olbermann has also long been linked to basketball star and ESPN analyst Rebecca Lobo. According to The U.S. Sun, the two dated around 1995, when Lobo was a UConn and WNBA standout and Olbermann was already a prominent ESPN personality. Neither has given detailed public commentary about that relationship, and most references frame it as a brief mid-’90s romance rather than a long-term partnership.