Holly Hester and David Letterman: Their One-Year Affair

by Amy Judd | October 3, 2009 at 08:03 am
7455 views | 20 Recommendations | 12 comments

Holly Hester was an intern on the David Letterman show in the 90s while she was attending NYU, and she came forward yesterday and said that she and Letterman had a one-year-affair. (Holly Hester pictures)

David Letterman asked her to the movies and that sparked off their romance.

"I was madly in love with him at the time," Hester told TMZ. "I would have married him. He was hilarious."

Photos

Late Show  | Photo 03

Late Show | Photo 03

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Holly Hester said that Letterman ended the affair because the age span was too great.

Holly's story comes one day after another former staff member, Stephanie Birkitt, said she had an affair with Letterman in 1996, who then paid her tuition at Cardozo School of Law. Their affair ended when Letterman's son Harry was born in 2003 according to the New York Post.

However, Birkitt also lived with Robert (Joe) Halderman who has been charged with trying to extort $2 million from Letterman. Halderman was a former CBS news producer; he has been issued with a temporary order of protection and cannot go near David Letterman. He has pleaded not guilty.

David Letterman told millions of viewers on Thursday night that he had sexual encounters with women on his staff.

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0
Mary Richard

Hey, as long as she was over 18, who's business is it but theirs?

Halderman's big plan is backfiring, badly.  All because of greed ..




0
Sandy L

Kudos to Dave for not being bullied into this extortion! HiFive to him for coming out with the situation on tv rather than taking the cowardly way of denying what would eventually become a tabloid sensation for the sake of  his self perceived public image.  If more celebrities would take Dave's cue the tabloids would be out of business!

1
Rory Cripps

Amy: I love these kind of stories! Thanks! LOL!

1
Professor Asus

These apparent trysts occurred years ago ...way before his current marriage...

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Rory Cripps

I never really understood David Letterman's success. I have no problem expressing genuine laughter and I can honestly say that I laugh often. But I just don't get David Letterman . . .in my opinion, he's just not funny. Have you noticed that his socks never match the rest of his attire and they often stick out like a sour thumb? At times it looks like he's wearing white Gym socks when viewed from a distance. His socks are definitely incongruous to the rest of his attire. Letterman's frank admission, on national TV,  that he has had sex with members of his staff, is an admission that would have probably been better off aired in a different venue. To me, Letterman never had class . . .and his recent remarks have not done anything to change my opinion.

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Amy Judd

I think he did the right thing by admitting it out loud in a public forum - I don't know if it should have been in a press conference or on his show, but I think he was right to face it head on. It was going to come out soon anyway and this way at least he can say he isn't hiding behind anything anymore.

Can't say I've ever noticed his socks though! I don't watch his show, except when Madonna was on it the other night!

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Rory Cripps

Amy: I understand why Letterman admitted it out loud in a public forum. It's probably something that he sincerely wants to go away as soon as possible. I had a problem though with the applause as he was relaying his version of the story to his audience . . . . I, if I were Letterman,  would be quite embarrassed. I didn't see any regret or shame in Letterman's face. I guess that I'm just a freakin' prude! LOL!

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Amy Judd

Oh I didn't see the video to be honest - it keeps getting taken down!

2
linda gravent

I know, right? A man of class would pay a little more attention to the sox and not so much to the sex!!!!11!!

0
HTuttle

Honorable, honest people have relationships with others who are NOT dating another, NOT married to another, NOT staff underlings...There's NOTHING to accept about all of this. ALL involved are lower level humans deserving NO respect.

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Dunston

What is it about women that makes them want to talk about who they were involved with? I'm not knocking Hester and everyone else who feels compelled to do this, but it's a pathology that most men don't have.

1
Mil

He is a despicable human being. What about the 22 year relationship he has had with his now wife and mother of his son? Look at him. If he weren't rich and funny, he couldn't even get a Billy Goat!! Stop passing this off as something noble. This is why society has become the way it is.

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Mary Richard
First Flagged at 8:38 AM, Oct 3, 2009 by Mary Richard
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