Sean Hannity and Ainsley Earhardt – Years Undisclosed
While this relationship has never been officially confirmed by the Hannity and Earnhardt themselves, the rumors about these two dating have been going around for some time, with colleagues saying they’ve been acting like a couple. This was almost roundly confirmed when the two showed up to Pete Hegseth and Jennifer Rauchet’s wedding at Trump International Golf Course together.

It’s said that they made a pretty grand entrance, showing by helicopter and making what many described as a grand entrance. Ironically, both of them had gotten divorced in 2019, coinciding with the timeline their rumored relationship had been active since.