Margo Howard | 10/09/2009 2:00 pm

A Letterman Update: More Information, More Thoughts, by Margo Howard

Editor’s Note: A longtime journalist, Margo Howard went into the family business (her mother was the fabled Ann Landers) in the 1990s as Dear Prudence. Her broad experience and understanding of human nature provide answers for the troubled — and entertainment for everyone else. Margo’s advice column, Dear Margo, appears twice a week — on Thursdays and Fridays — on wowOwow.com.

Well, now I think Dave has real trouble. It has come to light that the young assistant at the center of the Letterman/Halderman drama was being paid $200,000 a year and was sent to law school, courtesy of Letterman, with the promise that she would become his personal attorney. A guy can always be in the company of his attorney, right? Then it appears she was taken on trips “with the family,” with Regina none the wiser.

Now my guess is the humiliation is too overwhelming to overlook. My earlier thought was that the Lettermans would work it out, but now I ain’t so sure. I still think young Harry is the glue in that marriage, but he wouldn’t be the first kid to go between Mommy’s house and Daddy’s house. Were Regina to write me, I would encourage her to opt out of this humiliating arrangement and, as they say, take the money and run. I have no idea what their prenup says, but he is loaded, and given what’s gone on, her life would continue as lavishly as before. The guilty party is quite evident here … plus, the mother gets the kid, no question.

There is just so much a girl can put up with, and with each revelation he is looking more like a skunk. I wrote my previous piece with the information I had. Knowing what I know now, I am no longer sympathetic. It is quite clear that Dave, like many another middle-aged guy, cannot resist the chase and, alas, 20-some years with one woman has become totally boring to him. A pity. I believe that in any real sense he has already lost the cozy family of three, and if more drek comes out, he may lose his show. Stay tuned.

116 Reader Comments (so far…) Sign In or Register to comment

Look, why condemn him, he has only done what men do, screw around. His wife waited around for 20 years to marry this man and if she felt he was Mr. Notdoinganythingwithanybody then she was not living in reality. She had a baby late in the relationship for glue…well fine but now reality is in her face. I do feel for her though, this is embarrassing to find out that the woman that came on the trips was his lover. Oh well not the first man to do this and will not be the last. The woman was a willing partner, whatever her reasons. Oh, did she finish law school?

By T. BYNUM on 10/12/2009 10:42 am

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You will love Merrill Markoe’s comment- look at her response to comments number 4.1

http://merrillmarkoe.com/okay-here-it-is-my-big-comment-on-mr-letterman

By V B on 10/12/2009 11:10 am

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Of course the guy’s a scoundrel for having been so unfaithful to his wife. But I don’t feel comfortable telling his wife what to do. I know what I’d do in her situation, but if she does something different, then she has her reasons.

By M C on 10/12/2009 12:48 pm

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Things like this seem to be the normal in hollywood/politics these days.

Shame of these people for ruining other peoples lives and being self and only thinking of themselves. If Regina had not be told of any of these affairs and has been left in the dark about all of it then she should leave him and let him be left in dark by himself. He has only thought about himself and any woman that had an(affair) with him was only being selfish also. It also sickens me that shows/magazines sensationalize these parts of many peoples lives without any regard to who they are hurting.

By BARBARA SKINNER on 10/12/2009 1:55 pm

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It’s the "National Enquirer", but still, sometimes they are right - and they are reporting that Regina is seeking a $200 million divorce. Good for her!

By elaine s on 10/12/2009 2:27 pm

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The truth is this is none of our business what so ever! But, it’s such a great gossip because we all feel like we really know David Letterman. I feel sorry for everyone involved in this mess. I think we late night TV watchers over the years wanted to know why Letterman was always oddly withdrawn in many ways unlike most Late night talk show hosts that let you in to their world slowly but surely. He was obviously hiding his affairs from all the women that he was seeing at the same-time. It sounds to me like he was very much in love/taken with young Stephanie Birkitt to do all that he has done for her.

But, I remember once, a guest asking him what sparked him to finally marrying Regina after all these years, and Letterman answered that his son Harry had asked him to marry his Mom numerous times, so he did. I found that odd, but honest in the way when he answered that question. I feel badly for Regina his new wife/long time girl friend because she has been played as a fool. And, his son Harry someday will learn what a real cad his Father really was. Everyone suffers here! But Letterman is NOT a politician and his behavior happens a lot in all businesses everyday, every-week, and every year! This behavior will never end because people are fallible in their lives!

By Janna S. on 10/14/2009 12:46 am