A deep dive into Tapper's past reveals that he once dated Monica Lewinski and reported on it in a January 30, 1998, article written for the Washington City Paper. The article, titled "I Dated Monica Lewinski: Behind the tawdriest of headlines, there's a woman I wouldn't mind bringing home to mom" came out only 13 days after Drudge Report broke the story that Lewinski and then-President Bill Clinton had engaged in an sexual relationship between 1995 and 1996. In the article, Tapper talks about meeting Lewinski in a bar when he asked her for a quarter to continue playing pool. Tapper asked one of his Washington friends named Joe in the bar about Lewinski. "Joe told me that Monica was bad news, that she had left the White House because she had kept wandering into the Oval Office and inappropriately striking up conversations with the commander in chief," Tapper writes.
Figuring Joe was just spreading gossip, as was normal in D.C., Tapper and Lewinski exchanged information and set up a date. About the date, Tapper writes, "I didn't work her over for her opinions on Netanyahu, the emotional residue from her parents' split, any of that. It was a first date, one I wasn't sure would be followed by a second, and how was I to know that the woman on the other side of the table would set the presidency into seismic rumblings?" Now, nearly 20 years later, and being a regular fixture of network television, it would be a good story to say that you went on a date Jake Tapper, too.
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