The veteran talk show host first hit news at the end of last week with reports surfacing about an alledged extortion case against Letterman via a former employee of the network.

Now Letterman apparently had a fling with an intern back in the 90′s who she says “was madly in love” with Dave. Holly Hester, the woman making the claim, says Letterman and her dated for quite some time without anyone on the staff having the faintest idea. The relationship was apparently broken up because Dave said the age span was just too great.

All this material has set up plenty of opportunities to rub it in on Dave, creating material that is even better than the whole Sarah Palin fued.

Former late night talk show rival Jay Leno didn’t waste a beat to rub it in.

As always we turn to our TPH audience to help sort out another celebrity mess.

How big is this whole extortion deal and what do you make of the inner-love conspiracy?

Will this destroy Letterman’s legacy or will people forget about it after a couple of months?

When does a joke cross the line?

For Alaska Governor Sarah Palin, that’s when you make jokes about her 14 year old daughter. And she’s got a point.

“Late Night” host David Letterman on Monday poked fun at Palin’s visit with her family to a New York Yankees game this past weekend. “There was one awkward moment during the seventh inning stretch,” Letterman remarked. “Her daughter was knocked up by Alex Rodriguez.”

Letterman also said the hardest part about the Palins’ trip to New York was “keeping former New York Governor Eliot Spitzer away from her daughter.”

Palin said the comments, “crossed the line.”

“I would like to see him apologize to young women across the country for contributing to a culture that says it’s OK to talk about statutory rape,” Palin told the “Today Show.”

The major mistake Letterman and/or his writers made was confusing Palin’s daughter Bristol (the one “knocked up) with Willow, 14, the one who actually made the trip with the Palin’s to New York.

Palin doesn’t accept Letterman’s excuse for confusing the two daughters, “You and anybody else are extremely naive to believe their convenient excuse,” she told Lauer. “It took him a couple of days to think of that excuse. Regardless, it was a degrading comment about a young woman.”

“During the campaign, Obama said family is off limits,” Palin continued. “The ‘candidate who must be obeyed’ adhered to that,” she said. “But they haven’t done that on the other side of the ticket. So that’s a political double standard.”

On Wednesday night’s “Late Night,” Letterman addressed the audience for nearly eight minutes.

“We were, as we often do, making jokes about people in the news and we made some jokes about Sarah Palin and her daughter, the 18-year-old girl, who is — her name is Bristol, that’s right, and so, then, now they’re upset with me,” the comedian said then.

“These are not jokes made about her 14-year-old daughter. I would never, never make jokes about raping or having sex of any description with a 14-year-old girl,” he said, looking directly into the camera. “I mean, look at my record. It has never happened. I don’t think it’s funny. I would never think it was funny. I wouldn’t put it in a joke.”