Letterman is shown on Oct. 1st. Images thanks to Fame Pictures .

The timeline in the whole David Letterman extortion/affair/scandal has been rather fuzzy regarding when he was cheating with staffer Stephanie Birkitt. Dave was married to his longtime girlfriend Regina Lasko last March. One of the big questions was whether or not he was seeing Birkitt when he was married, which is still unclear. But he was definitely seeing her within several months of his marriage. Last fall he and Birkitt spent time vacationing at his Montana ranch – the same place he married Lasko in March. Tacky for sure. The NY Post (via PopEater) has a bunch of other interesting details as well.

Not long after David Letterman made a public apology during Monday’s episode, more scandalous details about his affair with ‘Late Show’ staffer Stephanie Birkitt started to surface — including diary excerpts about their sexual relations.

Birkitt’s diary revealed that she and Letterman enjoyed romantic hikes last fall at his sprawling ranch in eastern Montana — where he was married in March — while her boyfriend Robert “Joe” Halderman stayed home in Connecticut, sources told The NY Post. While she tried to keep it a secret, Halderman eventually found Birkitt’s diary in December and learned she was still carrying on a steamy affair with Letterman.

At the time, Birkitt, 34, insisted to Halderman that she and the 62-year-old Letterman had just “a platonic relationship,” a source said. “I’m his best friend,” Birkitt allegedly told her worried beau. Letterman would also drive Birkitt home to Norwalk, Conn., where she had been sharing a house with Halderman since he divorced his wife in 2004, sources said. The comedian lived with his longtime girlfriend and their son in Westchester.

Even after Birkitt graduated in June 2008, Letterman offered her a job as his personal lawyer. According to sources, Birkitt used the offer to persuade Halderman to have children with her, saying she would bring in the bucks with her new job and he could stay home. He and Birkitt had stayed together until last month, when they split up and his financial and emotional turmoil hit a breaking point.

[From PopEater]

Who are these sources? I understand that a lot of tabloids don’t print their names, but at least give us something to back up that they’re reliable. It all sounds legit to me, but more than anything I’m curious about who would have such detailed information about something that was a secret. It sounds like it’s coming from someone who has access to Birkitt’s diaries. I’d think if she told any friends about the affair, it might have come out already.

It makes me wonder if the leaks are coming from the D.A.’s office, or if perhaps someone in Robert “Joe” Halderman’s camp is spreading the information to make Letterman look bad. And to be fair, he already looks bad, though I believe he’s handled this whole thing as gracefully as possible. But he doesn’t look like a beacon of morality or anything. But since he’s the victim of an extortion attempt, people are obviously on his side versus Halderman’s. I imagine that Halderman and his bumbling lawyer, Gerald Shargel, could be getting desperate for some public sympathy.

Obviously none of this makes Dave look good. It’s awful of him to get married in the spring at the same place he had an affair in the fall. How could he go there and not be reminded of Birkitt? That’s what bothers me the most. It’s safe to say more sordid details will come out, but I think that as long as Dave continues to handle it well and move on, he’ll probably escape relatively unscathed. But I can’t imagine how his marriage could last.