"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.
Letterman's particular situation, of course, is far from ideal. He reportedly engaged in sexual affairs with staffers while also dating Lasko. On his show last night, the host acknowledged the pain he had caused Lasko, with whom he has a son.
"She has been horribly hurt by my behavior, and when something happens like that, if you hurt a person and it's your responsibility, you try to fix it," he said. "And at that point, there's only two things that can happen: either you're going to make some progress and get it fixed, or you're going to fall short and perhaps not get it fixed, so let me tell you folks, I got my work cut out for me."
The fact that Letterman dated more than one staffer also complicates matters, said Lisa J. Banks, a partner with the Washington, D.C., employment law firm Katz Marshall & Banks.
In an office in which a boss makes a habit of dating staff, other employees may "fear (they're) the next target," she said.
Other ways fellow employees may be affected by a boss-subordinate romance include the perceptions that the boss is favoring his or her romantic partner when it comes to work assignments or salary.
Sometimes such perceptions aren't unwarrranted. The National Human Resources Association's Murphy said that, at a previous job, she once had to fire two employees after one, a supervisor, falsified his girlfriend's timecard so she got paid for time she hadn't worked.
To avoid favoritism and the perception of favoritism, Murphy recommends that boss-subordinate couples should work to provide some distance between one another at the office.
Once they've determined that they're in a relationship for the long-haul, she said, it makes sense to disclose the relationship to a higher-ranking supervisor and request that one person be assigned to a different department so that one no longer has power over the other, she said.
Losee noted that some companies even ask dating employees to sign "love contracts" -- contracts where employees agree that their romantic relationships are consensual -- in an effort to shield themselves from sexual harassment complaints down the road.
Banks said that in at least one sense, at least, Letterman's office romances could be considered successful because they didn't end in sexual harassment complaints.
There's been no suggestion that any of his relationships have been "unwelcome," she aid.
"People can criticize him for many things related to this, but it doesn't appear that sexual harassment is one of them," she said.