Don't get me wrong, it's fantastic when things are going well. Picturing that hot security guard naked is greatly improved when you can actually rip his clothes off later. Sex breaks make a workday go by like THAT, I'll tell you. But, oh man, if things go south, we're talking Antarctica, folks.
There are some strong-willed individuals that can take it in stride, but most end up in a drama that could be in contention for a daytime Emmy. You not only have to see the person every day, you have to interact with them in this smooth, detached way, when what you want to do is run away or scream or cry or punch them in the face.
Letterman's situation is complicated further because the women he slept with worked for him. Bonking the boss brings up issues surrounding coercion and favoritism, either real or imagined. There's also a real power imbalance in a relationship like that, no matter who is in the boss role. When you can punish your partner professionally for something that happened in your personal lives, it skews things.
So I say proceed with caution, whether it's the boss or a colleague. Getting into a situation that could ruin both your personal and professional life in one fell swoop is not something to play with, no matter how delicious that situation may be. I say find yourself someone from another inkwell and use your imagination. One day you're the boss, the next day you're the personal assistant, the next the copy repair person...the fun is endless!!
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