Ask a Badass is an advice column answered by history’s hidden badasses, writing as they see their whole lives and our modern world.
I’ve been having fantasies about my co-worker for a long time now. She picks up a cup of coffee? It’s the sexiest thing in the world. She says my name? It makes me melt. Do you think I should tell her, or should I keep up the professional boundary and keep my fantasies to myself?
Longing and in Pain
You’re in a tricky spot and the stakes are high. Lucky for you, your question got to the right person. Can you imagine a workplace more cutthroat than a pirate fleet? And I married not one, but two of my fellow pirates. I love the spot you’re in, but then I always loved the height of a gamble, when the tiles are in the air. It’s like the moment before a first kiss when anything is possible. I’ve lived my life by upping the ante every chance I get, and it’s worked quite well for me. I was born into a brothel, and I’ll die a rich and titled woman. However, you asked for advice and a good madam tries to provide what she is asked for.
You need to start by figuring out the stakes. What could your losses be? The obvious is your professional reputation. Every field has a code of conduct and most modern ones exclude drooling on a colleague’s shoes. I had a strict code of conduct I made every soldier in my fleet adhere to, with beheadings for first infractions. Harsh, yes, but what other pirate could say that orders were never disobeyed, and female captives were unmolested? I’m sure your boss won’t behead you, but you should imagine what your boss would say about your office conversations. Don’t say anything in the office your boss couldn’t overhear.
This brings me to the dicier stakes. Your letter is redolent with your feelings but says very little about your coworker. Do you have any sense of how she feels about you? Does she already know how you feel? If so, her silence is an answer. If not, you will need to be very careful that she leaves your encounter with no cause for complaint. A fractured crew cannot work in unison and an unwanted romantic overture can cause great discomfort. All of your actions, for some time before and after, will be viewed through the lens of your attraction.
Now, do you know what is to be gained? It sounds like you are enjoying your fantasies quite a bit. The pain of longing is quite a delicious one indeed. Are you entirely clear that you actually want to act on your fantasies? Will opportunity make the allure of the forbidden disappear? Our fantasies are made of glamour and our own ideas. Human lovers are their own, entirely independent beings. Do you want to be with that being, or will reality chase away your fantasies?
If you are certain that what is to be gained is worth more than what is to be lost, you need to develop a strategy. When I lead the Red Fleet to victory over a joint gweilo and imperial navy, everyone wondered where a prostitute had learned strategy. As if out-navigating mismatched generals was more complicated than taking sole control of 70,000 pirates who saw me only as my husband’s widow!
The most important advantage you have in any encounter is the terrain. A professional environment is ill-suited to your needs, so I suggest a change in venue. Near the end of the day, casually ask her if she wants to grab a drink or coffee. Her answer will give you all the sign you need. First and foremost, you must accept a ‘no’ as final. Trying to negotiate your coworker into a date just makes you look sad and unprofessional. If she says some other time, wait for her to bring it up again.
The same rules apply if you do go out for drinks. Take no as a no, a maybe as a sign for her to make the next move, and a yes as an enticement to create many more yesses.
May you be as lucky as you desire.
Born around 1775 in Guangdong Province, presumably in difficult circumstances. Died in 1844 in Canton as the wealthy proprietor of a popular gambling house. The woman who was to take the name Ching Shih was a prostitute in a floating brothel when she married Cheng I, the captain of a large fleet of pirate ships. They spent six years together growing the fleet and when he died, she took control of the pirate armada and married Cheng’s second-in-command. They so dominated the China sea that even the full weight of the combined British and Chinese navies were powerless to stop the red sail fleet. She negotiated an amnesty for herself and her fleets that allowed her to keep her wealth and made her husband a lieutenant in the Chinese navy. There are no portraits of her, but the sketch above was made during her lifetime.
For a fun article on Ching Shih, check out Smart Bitches, Trashy Books.
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