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David Letterman's Other Other Woman

10/5/2009 10:00 AM PDT BY TMZ STAFF

TMZ has obtained photos of Holly Hester -- the woman who acknowledged she had a relationship with David Letterman in the early 1990s -- back when she worked as an intern for Dave.

David Letterman's Other Other Woman

The pics show Hester with segment producer Frank Gannon (top) and writer Joe Furey (bottom) and were taken in Dave's outer offices back when he was at NBC.

Hester said her relationship with Letterman lasted a year and that she was "madly in love with him."


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The network should SMACK his hand hard for "fraternizing" in the workplace. It will be interesting to see what they do over this. I heard on the news last night that tv networks take this sort of thing very seriously. I wonder how "SERIOUS" they will take it consider this is Mr. Moneymaker "King of Late Nite"?! lol! So I guess, if he has been with his wife for the last 23 years(living together), yet only just married in March; it would seem that Mr. Letterman obviously has a bit of a "commitment" problem? For him to have brought this out in the open, hopefully this is a problem that he has dealt with & resolved? Hope so for Mrs. Letterman's sake. She seems like a VERY private person too. I bet she just hates all the attention this is going to bring her way. She won't even be able to leave their home. Bet the paps are already camped out, outside her window! lol.

I think Letterman is a bit pompous & arrogant but he IS funny as hell! You've got to give him credit for the way he outed himself. That's pure GENIUS & is clearly the reason why he's considered the 'King'. YEAH! Try & take Letterman's money will you 'Mr.48HRS-man'!! lol I LOVE IT!!!

1844 days ago

whats up Doctors    

30. So what's the big deal? He asked if she wanted to date. She accepted and they had a good time, then he broke it off. There was no force...nothing.

Leave David alone. NO story here!

Posted at 7:05AM on Oct 5th 2009 by Vicki

Holly Hestr was a girl Dave dated about 20 years ago, the went there seperate ways.Hideous Not,Harv who were you dating 20 years ago? Say it is'nt so lol

1844 days ago


Letterman sure likes 'em homely

1844 days ago


Well it appears old Dave likes them dogs.Woof Woof.

1844 days ago

Kooky Fan    

Dave you is a dog. I hearz you like to floss 'dem gap teeth with intern pubic hair - YOWZA!

1844 days ago


Letterman is a pervert and should be FIRED. Imus got worse for NOTHING. IF there was an extortionist in this matter, IT WAS LETTERMAN EXTORTING SEX FROM INTERNS. He extorted sex from them because they were vulnerable since he was their boss and they wanted to be in television. Letterman forced those interns to give him sex in exchange for NOT FIRING THE INTERNS. That IS EXTORTION.

1844 days ago


Seriously....why is this news? Here's a tidbit for you TMZ: Most men in powerful positions have sex with their staff members. We may criticize and judge all we want, but those are the facts. It takes personality, confidence, charm and determination to get into powerful positions and these are the same personality traits that attract the ladies. It has been that way since the begininning of time. This is hardly scandalous and hardly newsworthy. Nobody was married, and even THEN it is still none of our business! So there....sorry to have killed your big future stories. You probably had sting operations going on at all the talk shows trying to catch some more consensual adult sex going on.

1844 days ago


mind your grammar TMZ. your credibity is falling and your story about Maya Angelou being hospitalised is totally false.

1844 days ago

Money Talks    

It is beyond me how a young woman can have an affair with David L. I mean he is not attractive at all. Oh ! I forgot, he has power and also $$$$$$$$$. There is a lack of ethic on his part to profit from his position. As for the women who slept with him and 'were madly in love with him (sic and sick)' what is there to say. When will this nonsense about sex, power and money stop ? Things are going too far.

1844 days ago


Ya know...I have not been a big Dave fan ever since he decided to spew his ultra liberal views and opinions all over his show...but on this issue I must say...who cares, it happened along time ago, he has moved on with a wife and a kid ...let's call it a day and moce on also!

1844 days ago


Um.. this was back in the 90's. WHo cares.

Someone posted "Dave'spoor wife and child." Why? Because he dated people before they were married and before his son was even a thought or born?

People you need to get a grip.

Who hasn't dated before they got married? Everyone has a past. I don't see why whom Letterman ever dated should be so interesting and such an issue.

Get over it. Nothing to see here.

1844 days ago


Dave has cruddy taste!

1844 days ago


I remember her! I always felt sorry for her. Once, Dave had her dress up like Little Bo Peep and go out on the street to ask passers-by if they had seen her sheep.

1844 days ago


I never knew that the MAD Magazine guy was a stud!

1844 days ago


who carers more mj news now!!!!!!!!!!!!!

1844 days ago
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