That Time Jake Tapper Dated Monica Lewinsky

The wave of high-profile sexual assault and harassment accusations permeating Hollywood, D.C. and beyond over the last few months has led to some relitigation of the power dynamics in older cases of sexual misconduct, including the famous Bill Clinton/Monica Lewinsky scandal.

Re-opening that discussion also unearthed an already public but fascinating tidbit from the late 1990s: A few weeks before the Clinton/Lewinsky story broke, CNN Chief Washington Correspondent Jake Tapper went on a date with Lewinsky.

Tapper even wrote what is essentially an oral history of their date in the form of a 1998 Washington City Paper essay with the appropriate headline, “I Dated Monica Lewinsky.”

But before we get into the sordid details, let us remember why that article is relevant in 2017.

How the Tables Have Turned

Former Hollywood executive Harvey Weinstein’s predatory behavior toward women and the subsequent reporting exposing other men’s similar transgressions have led some to believe that what Clinton did to Lewinsky was a clear abuse of power by the most powerful man in the United States.

A new question has surfaced regarding Clinton’s behavior: Have we given Clinton the political treatment in terms of sweeping his sexual infractions under the rug?

And these are not just the usual voices from the right calling for liberal comeuppance; the new anti-Clinton voices include the likes of Democratic New York Sen. Kirsten Gillibrand and the left-leaning Vox.

According to the New York Times, “Asked directly if she believed Mr. Clinton should have stepped down [when he faced his own allegations as president], Ms. Gillibrand took a long pause and said, ‘Yes, I think that is the appropriate response.’”

To underscore why that statement is a “big deal,” the Washington Post’s Aaron Blake broke down its potential ramifications for Gillibrand’s political career, especially any 2020 presidential aspirations she may have.

“This stance would seem to have the dual effect of distinguishing her on a very important issue in that race, but also of potentially alienating the many well-heeled and influential supporters and donors she has in common with the Clintons,” he wrote.

Vox’s Matthew Yglesias took a similarly harsh stance in an article with the blunt headline, “Bill Clinton should have resigned.”

“Republicans prosecuted a bad case against a president they’d been investigating for years,” he wrote. “What we should have talked about was men abusing their social and economic power over younger and less powerful women.”

When Tapper met Lewinsky

With that context, now we can focus on Tapper’s 1998 essay about his relationship with Lewinsky.

In December 1997, the then-28-year-old Tapper met the then-24-year-old Lewinsky at Stetson’s on U Street (now Exiles Bar).

Their date took place on Tuesday, Dec. 23, at “Roxanne’s, a nice Tex-Mex place” in Adams Morgan (which appears to still be a thing!).

“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,” Tapper wrote. “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 dissected what he was able to glean of her personality: “She struck me as cheerful, open, a bit too much a resident of Planet Hap-Hap-Happy in my acerbic view. A little bizarre in her almost childlike sweetness … but she was from both L.A. and money, so her unusualness had a context.”

Tapper also described her looks, which, well, judge for yourself: “Physically, she was pleasant without being overwhelming. She’s a little chubby, but she’s leaps and bounds prettier than that vacuous mugshot beamed all over the world.”

Side note: I accidentally called Tapper out on his language regarding Lewinsky’s looks via Twitter, and he responded as such:

Overall, Tapper said she was “a sweet girl. Nice,” and thought maybe they would go out again. New Year’s and vacations got in the way of planning a second date, and before they could get together again, Matt Drudge revealed Lewinsky’s affair with Clinton to the world on Jan. 19, 1998.

“My sum total experience is a meeting of eyes at a boring bar party and a B-minus date afterward,” Tapper wrote. “If fate, Vernon Jordan and Ken Starr hadn’t intervened, who knows, maybe I’d be the only reporter in the world pursuing her.”

The Scarlet Letter

Salacious details aside, Tapper’s account also proved prescient to the way Clinton’s misdeeds are being discussed today.

“Monica was/is like a lot of young women inside the Beltway, only more so: young, ambitious, and looking — looking for next, seeking a place to land, searching for that one friendly face in the crowd who will think she’s worth talking to,” he wrote in 1998. “A guy, a boss, a boyfriend, a mentor, a friend.

“For Monica, that person turned out to be Bill Clinton,” he continued. “Clinton apparently saw in her either a consummately gullible kid, or maybe, just maybe, he was taken by the same thing I was: an absence of jade, a willingness to look around the next corner, a sweetness that is rare in a city built on bitter and sour and salty.”

Tapper continued his defense of her and condemnation of men abusing their power in a 2016 interview with The Hill’s Joe Concha, also blasting the public response to the scandal surrounding then-Gen. David Petraeus sharing classified information with Paula Broadwell, his biographer and mistress.

“That is an odd thing for society to debate and discuss,” Tapper said before making a Scarlet Letter reference. “The woman gets the Hester Prynne letter and Reverend Dimmesdale gets to go and preach.”

Based on those statements, Tapper may appreciate how public opinion is turning on Clinton thanks to a newfound societal distaste for men who use their positions to take advantage of women (or men for that matter, à la Kevin Spacey).

Not that this national awokening erases the two decades of bullying Lewinsky has endured. But at least it’s a start in preventing other women with similar stories from being treated that way.

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