8 Reasons I Sympathize With David Letterman

The series of office romances was a perfect storm for infidelity.

dave letterman

OK. So you already know the deal with Dave Letterman. If not, please check out this: Details Of The David Letterman Sex Extortion Case

And this: Letterman Blackmailed For Revenge? Diary Tells All

… for the recap.

It's some heavy dope, mang. We'll probably never know the full extent of what went on because Letterman is such a private dude, but we can likely assume that a few of these allegations are factual and actual. And guess what? I'm really having a hard time seeing the overwhelming wrong in all of this.


Dave Letterman has been with Regina Lasko since 1986, it's said. Given his penchant for privacy, we really only know that the couple has a 6-year-old son and have been legally wed since March of 2009. I was sort of hoping that it would be revealed that his extracurriculars ended after his heart surgery in early 2000* or at least the birth of his little man in 2003. At least he said he was sorry, right? Read: 3 Ways To Handle Infidelity Like A Celebrity

What I do know is, that while I don't condone cheating, as Chris Rock says, "I understand." The Letterman romance situation is/was a veritable perfect storm of opportunity (in no particular order):


1) Dave's company, Worldwide Pants, produces the Late Show, not CBS. Their HR policies are likely to be more liberal than the network's, per Examiner.

2) Dave was unmarried until this year and his home, Connecticut, does not recognize common law marriage. Maybe their subdued March wedding was to end certain dalliances. Read: Cohabiting Rights May Come To A State Near You

3) Dave is usually regarded to be a pretty good guy. He's personable, self-deprecating and generous (or charitable), which chicks dig. Also, it's been said that he's discreet and gentlemanly about his pursuits. Read: Is It Better For A Man To Be Funny Or Rich?

4) Late-night television requires long hours and tons of interaction between team members. They shoot five, one-hour (44-minute) TV shows in four days. Plus they do this roughly 40 weeks per year. Conventional TV and films are like 9-to-5s by comparison. Read: The New Hook-Up Hotspot? Work!


5) The on-site suite. Rumor has it that Letterman has a suite in the Ed Sullivan Theater in addition to a nice office. "One thing leading to another" is a lot easier when an option other than a bathroom stall, a desk or a leather office couch exists. Read: Guide To Getting Lucky In The Lavatory

6) He's a legend. Having someone like Letterman interested in you, even platonically, has to be a huge ego boost for a twentysomething woman in television.

7) Dude is 60+. See #4, comedy is a young person's game. Being around (and periodically, in) young people is the best way to stay young (plus exercise and anti-oxidants). Read: Age Differences: I'm 22, He's 35. Can This Work?

8) It seems like an "understanding" with his wife could exist. While we'll never know this, it just seems like you'd have to have some kind of arrangement to date someone for 23 years before getting married. Especially if the last 6 years involve a kid. Read: Tilda Swinton’s Odd, Um, Arrangement


While I'm not saying I condone or agree with anything that took place at the Ed Sullivan Theater (and beyond), I can see why and how it went down. And, though I think quite highly of my moral fiber, I can't say that I wouldn't do the same thing in the same situation (either as Letterman or a piece of man candy working for Chelsea Lately). It seems too easy to cast the first stone when few of us have ever been tested in the same way. Maybe it's just easy for me to see this from Letterman's point of view because he looks like my dad.

Cheers, jeers, bring 'em on.

*Note: I had a good friend who interned for Letterman during the spring semester of 2000, just before and after his bypass surgery, who claims that Letterman was a different guy as a result of the procedure. I was hoping that his brush with mortality was the thing that made him give up the ass-on-the-side. Maybe not.