It appears that Katie Couric and Larry King Live were once almost a couple. Or at least they could have been, if King weren’t such a bad date when they went out once over 25 years ago.

Couric appeared on “Jimmy Kimmel Live” Thursday night, and during the interview, Kimmel mentioned that he heard she once went out with Larry King, when they both lived in Washington, D.C. Couric confirmed the story and gave one of the most hilarious “bad date” stories of all time.

According to Couric, she went out with Larry King some 26 years ago, when she was 30. Couric, who is 56 now, is 23 years King’s junior, so there’s quite an age difference involved.

"It was at one of these Italian restaurants where they put you right next to each other like they do all the men and their 'nieces,'" Couric said, adding: "We had a nice enough time and we're going home and I see that we're going over [Arlington] Memorial Bridge, and this is not the way to my apartment. I said, 'Larry, where are we going?' And he said, 'My place.' Oh mother of god."

Of that wasn’t crazy enough, it seems that King isn’t exactly the smoothest operator in the world. He doesn’t seem to understand the rule that you only make a move if you’re picking up signals from your date.

"So we sat there, and what can I say? He lunged ... and I started laughing a little bit because the whole situation was out of a bad Lifetime movie. I said, 'Larry, you are such a nice man, but I would like to meet someone a little closer to my age”

“Someone not from the Paleolithic era,” Kimmel quipped.

And in an even weirder alternate universe love connection, Michael Jackson was once interested in asking Couric out on a date as well. The two met briefly while Couric was hoping to score an interview with the pop icon, and while she didn’t get the interview, Jackson did later ask a mutual friend if she was interested in a date. Sadly, the Jackson-Couric romance was not meant to be, and she turned him down.

"Can you imagine going to my daughters, who were 8 and 4, saying, 'Honey, I'm going out on a date with Michael Jackson'?" she said. "But I'm sorry I didn't just have dinner with him because that would have been a fascinating conversation."

Watch a video of Katie Couric describing her date with Larry King on “Jimmy Kimmel Live” below.