Margo Howard | 10/09/2009 2:00 pm
A Letterman Update: More Information, More Thoughts, by Margo Howard

Image: Willem van Bergen/Flickr
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.
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.
Read more about: David Letterman, Entertainment, Joe Halderman, Margo Howard, Marriage, News, Relationships
























116 Reader Comments (so far…) Sign In or Register to comment
I suppose $200,000 for Dave is pocket change, but no matter. If he with held this information from his wife, he should be hung out to dry. Regina will not be living in the Motel Six by any means. She and her son would be well provided for. But only she knows what is the best course of action.
Dang… how many personal attorneys does Dave need? As if that was his true motive.
Do I just love hearing that I was right from jump street. We haven’t heard one third of this story yet. Hundreds of people are on the ground asking questions all day and night.
Like I said originally, he’s a pervert.
Maggie: He should be hung out to dry. Don’t you have some "splainin" to do? Bada boom bada bing.
C Hardy,
I so agree with you. Looks like mother and daughter who wanted to do the horizontal mambo with Davey are eating crow right now. I’m so glad that several on the previous post were against this creep and calling him what he really is, just a stupid scumbag! I wonder what "crow" taste like?
I would be willing to bet that when you change your mindset about something, you are not near as quick to admit that your opinion has changed. I give props to anyone who can say, "I have changed my mind now that I have more information." That is the mark of a wise, worldy person.
Having an opinion is not a matter of being wrong or right. There is no crow to eat here.
Mjit: Its called prostitution.
No one pays an assistant anything $200,000 a year even in Manhattan. Some of us did feel there was more to the story. Apparently there was.
As for the marriage, it was probably one of those "eyes wide shut" situations and I doubt the revelations themselves are the problem but the presentation of them so publicly by him. It may turn out, as I commented in Round One, that he would have saved himself some money by paying the blackmailer. And possibly returning the diary. Two people claiming someone was paid off because they were a nuisance is always better than one.
I still think it’s much ado about nothing and still am sympathetic towards all of them. Except the jealous lover who tried to sell the diary which wasn’t his to sell.
Wayyyyyyyyyyyy back, Letterman appeared to be absolutely full of himself, but that’s how sociopaths rise to the top, but all that can be replaced by baking powder! Our TV and print is full of this - we wonder what’s happened to those under 50, now? It’s obvious. He’s milking his perceived fans for all he can get, and dragged two innocents with him - it served him well to be a "father," but he couldn’t pull off the "daddy" stuff, or the husband role.
How men like that one can even dream of being Romeos, is beyond me!
Baby: So you actually believe that Lettermans wife didn’t care about him screwing everything that moved? He was doing young girls in their early 20’s. I’m sure his wife is just thrilled about it. I knew there was more to this story. Maybe one or two others.
No one pays an assistant 200K. Why not? Spitzer was paying Ashley Dupree 5K an hour. It adds up.
Whew, that girl seemed to be all about bidding wars when it came to partners! Pretty high priced all american girl?? Now will see which publisher she takes for a high bid for an inevitable book deal! She knows how to play the numbers game! She is probably already waiting for the suckers to line up.
As for David, what goes around comes around, and that just might include losing this game. How stupid could he get would be the question, but then you already answered that.