Letterman's past relationships with staffers came to light last week when, on his show, he alleged that a CBS News producer tried to extort $2 million by threatening to go public with information on the host's workplace liasons.
The news spurred ribbing from Letterman's late-night comedy peers as well as disaproval from critics who contend that relationships between bosses and employees are wholly inappropriate. Indeed, they can point to a slew of prominent examples of when such relationships -- sometimes in the form of extramarital affairs -- went awry, including those of former Sen. John Edwards, Nevada Sen. John Ensign, former WellPoint CFO David Colby, former Boeing Chief Executive Harry C. Stonecipher and President Bill Clinton.
Losee, the co-author with Helaine Olsen of "Office Mate: Your Employee Handbook for Romance on the Job," said that while she generally recommends against supervisors pursuing romance with their underlings, "at the same time, we are in no position to tell people what to do with their hearts."
Losee said that, the horror stories involving politicians and other famous figures notwithstanding, boss-subordinate romances often end in marriage -- 44 percent, according to a 2003 survey by American Management Association. That's not surprising, given the amount of consideration that often preceeds such relationships, she said.
"The risk is so much greater and people do give it a lot more thought before they get into" such a relationship, she said.
The sparks behind these and other office romances, she said, are similar to those in other relationships: common interests -- in these cases, professional interests -- and close friendships.
"You get to know this person under fire. You see them when they're challenged. You see them deal with colleagues. You see them when they're exhausted on a Monday and (you see) what is the content of their character," she said.
You know a great deal about them "before you ever go on a date," she said. "That's old-fashioned, not skeezy."
Noteable office romances that have resulted in marriage include those of Bill and Melinda Gates, Les Moonves and Julie Chen and President Obama and first lady Michelle Obama.
Melinda Gates, then Melinda Ann French, maried Microsoft founder Bill Gates in 1994, seven years after she started working for Microsoft. The Obamas married in 1992, after Barack Obama worked as an intern for his future wife when she was an associate at a Chicago law firm. CBS Corp. CEO Moonves married CBS "Early Show" anchor Julie Chen in 2004.
Letterman himself can be included in the from-superior-to-spouse club: His wife, Regina Lasko, whom he married earlier this year, was once also a staffer on his show.
Experts say there are also plenty of boss-subordinate relationships that fizzle but avoid major workplace drama in the process.
"There have probably been more success stories than there are times when it went bad," said Sue Murphy, the manager of the National Human Resources Association in New Hampshire.