Holly Hester was David Letterman's girlfriend for awhile in the 1990s. Holly Hester is one of two women (along with Stephanie Birkitt)...

by Free Britney at . Comments

With all the attention paid to Stephanie Birkitt - the former assistant David Letterman had an affair with, and whose cheating on Robert Halderman may have sparked the alleged extortion plot - Holly Hester has been all but forgotten.

She is probably grateful for this.

But the "other" other woman in Letterman's life sure was comfortable in Dave's offices back in the day, as some new photos unearthed by TMZ today show ...

Holly Hester Pic

Holly Hester at David Letterman's offices back in his NBC daze.

An intern on Late Night 20 years ago, Holly Hester says she had a secret relationship with the host when she was a student at NYU and fell head over heels for him.

She says they dated for like a year.

Like the first pictures of Hester we posted a week and a half ago, these are from the early '90s and completely innocent. David Letterman himself is nowhere in sight.

Click to enlarge some more photos of Holly kicking back at Dave's desk with one of his beloved cigars, and displaying some vintage '90s jeans near the office throne:

  • Holly Hester the Boss
  • Holly Hester Image
  • The Other Intern

by Free Britney at . Comments

Photos of Holly Hester - the second woman who acknowledged she had a sexual relationship with David Letterman in the 1990s - have been obtained.

The photos were obtained when she was an intern for Letterman.

Here's Holly Hester with segment producer Frank Gannon (top) and writer Joe Furey (bottom) at Dave's offices back when he was still at NBC ...

Holly Hester with former Late Night co-workers. [Photos: TMZ]

Prior to the Late Show with David Letterman's CBS debut in August 1993, the host starred on Late Night on NBC (he was replaced by Conan O'Brien).

His relationship with Hester took place prior to his move to CBS and lasted a year. Holly said she was "madly in love with him" but he broke it off.

He had a relationship with Stephanie Birkitt later in the '90s.

Letterman confessed that his affairs with staff members (how many, he did not elaborate) recently made him the target of a $2 million extortion plot.

Were they the only two? Or were these affairs just the beginning?

by Free Britney at . Comments

Yesterday, Holly Hester became the second to claim she was one of the women David Letterman slept with during the 1990s. She likely will not be the last.

Holly said she and Letterman were together for over a year in the early 90s, and that she would have married the hilarious late night comedian if possible.

Letterman in Action

She claimed to be with David Letterman just a day after the Late Show host confessed that someone was trying to extort him for $2 million over his affairs.

Letterman's affair with Holly Hester allegedly began when she was an NYU student and an intern for the show. A year-long romance ensued, she said, until the funnyman called it off because of their age difference.

A source close to the show tells the New York Daily News that the host kept a secret bachelor pad above his set in the Ed Sullivan Theater on Broadway.

"He doesn't have to come out," a staffer said. "He has a suite upstairs."

An ex-Late Show staff member said that Letterman kept a room insiders dubbed "the bunker" that was open only to his favorite young female underlings.

The allegations followed a similar admission from former Late Show staffer Stephanie Birkitt, who claims to have had an affair with him in the late '90s.

Stephanie Birkitt later spent years with Robert Halderman, accused extortionist of Letterman - which may explain how Halderman knew of Dave's love life.

Letterman, 62, admits that he had several affairs, apparently while dating longtime lover Regina Lasko, who he married in March. They have a son, Harry, 5.

Shocking as the allegations by Birkitt and Hester are, some believe they may be the tip of the iceberg. People alleges the existence of a third Letterman girl.

Whether that's true or not, rumors will likely continue to fly in the coming weeks regarding scandalous love affairs between Letterman and young staffers.

All of which puts even more pressure on Letterman.

When he devoted a 10-minute monologue on his show Thursday to the extortion plot and affairs, fans generally stood by him and appreciated his honesty.

But as more details of his actions become public knowledge, rumored or true, they begin to overshadow the extortion scheme. He may not be a hypocrite or have done anything illegal, but Letterman's reputation will take a bigger and bigger hit.

How he responds will be very interesting to see.

by Hilton Hater at . Comments

When David Letterman told the world about the extortion plot against him on Thursday night's Late Show, the host said he's slept with women on his staff.

In other words: it sounded very much as though Stephanie Birkitt was not the only employee to have sat atop Dave's Top 10 List... if you know what we mean!

Now, Holly Hester has told TMZ that she interned on the talk show in the early 1990s; long before Letterman was married or became a father to son Harry.

A student at NYU at the time, Hester says she and Dave went on a series of secret dates, a relationship that was unknown to anyone else on the staff.

"I was madly in love with him at the time. I would have married him. He was hilarious," Hester said, adding that the courtship ended after a year.

Clinton and Letterman

We can only imagine what Bill Clinton and David Letterman are laughing about during the former President's appearance on The Late Show.

Jay Leno, meanwhile, got in a friendly, harmless jab at his fellow host. When he came out for his monologue last night, the NBC star told the studio audience:

"Settle down. If you came here tonight for sex with a talk show host, you've got the wrong studio."

As we've said before, Letterman is NOT a hypocrite for sleeping with anyone on his show. As a hired, self-deprecating, admittedly imperfect entertainer, he's the opposite of an elected, two-faced politician.

Now that the joke is on the other foot, however, it will be interesting to see how he responds to digs at his expense.

Holly Hester Biography

The Other Intern Holly Hester was David Letterman's girlfriend for awhile in the 1990s. Holly Hester is one of two women (along with Stephanie Birkitt)... More »
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