Did Jake Tapper date Monica Lewinsky? Duo spill the beans during 'Impeachment' interview

CNN anchor Jake Tapper recently reunited on-air with activist Monica Lewinsky during an episode of The Lead with Jake Tapper and revealed that he once went on a date with her in late 1990. The duo reunited for an interview nearly 24 years after their date.

Lewinsky appeared on the show to talk about her latest venture as a producer of Impeachment: American Crime Story. The FX series is based on her infamous affair with former U.S. President Bill Clinton that led to his 1988 impeachment.

While speaking about an episode that highlighted Monica Lewinsky and Jake Tapper’s Washington D.C. date, the latter jokingly opened up about the real-life scenario from 1997:

“First of all, Monica. Yes, I have to disclose, full disclosure in tonight’s episode, our G-rated date from December 1997... is portrayed I should note by an actor way better looking than me now or then.”

Meanwhile, Lewinsky interrupted him to clarify that the duo only went on “one date” back in the day.

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Everything about Jake Tapper and Monica Lewinsky’s 1997 date

Jake Tapper and Monica Lewinsky went on a date in 1997 (Image via Getty Images)

American activist and TV personality Monica Lewinsky became a household name in 1998 due to her affair with Bill Clinton. She was reportedly in a relationship with the former U.S. President between 1995 and 1997 as a White House intern.

However, during the 1998 Paula Jones case, Clinton famously denied his relationship with Lewinsky in a televised interview. As further investigations disclosed the affair, Clinton was impeached for lying under oath.

The entire controversy has been documented in the FX series, Impeachment: American Crime Story. The fifth episode shows Lewinsky crossing paths with Tapper at a bar in D.C. before she departed from Washington for a fresh start in New York.

The pair started a conversation, enjoyed dinner together, and went their separate ways without taking the encounter any further. The film sequence was inspired by Monica Lewinsky and Jake Tapper’s real-life 1997 date.

Amid the highly publicized Clinton-Lewinsky, Jake Tapper opened up about his single date with Monica in a January 1998 article for the Washington City Paper. The duo first met at a party through mutual friends and later went to a Tex-Mex restaurant.

Tapper wrote that Lewinsky was different from other people he met at the time:

“Right off, Monica was different from the standard D.C. date: not a salad-picker, she joined me in appetizers and an actual entree of her own. She had a beer or two, while I drank bourbon. She even offered to pay for her share, a fairly rare offer I rejected but appreciated.”

He shared that the pair even discussed Lewinsky’s past relationships but did not talk about the President:

“We talked about some of her past relationships, though the president’s name did not come up. 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?”

Jake Tapper also mentioned that Lewinsky appeared to be “happy and cheerful” ahead of the looming investigations regarding her affair with Clinton:

“She didn’t strike me as a classic climber - just a woman looking for a decent, challenging job and a happy life to go with it. She struck me as cheerful, open, a bit too much a resident of Planet Hap-Hap-Happy in my acerbic view.”

The duo never met for a second date due to their busy schedules. Jake Tapper wrote in his article that he never expected to see Lewinsky again:

“I don’t expect to see Monica again. To be honest, I’m not sure I would have seen her even if she hadn’t ended up buried beneath the headlines.”

The pair finally reunited earlier this week and discussed the truth behind their single date. Jake Tapper is married to Jennifer Brown. The couple share two children.