I have a reputation for occasionally saying outrageous things, and things that I shouldn’t be saying. I frequently make people uncomfortable by saying what I say, including what I sometimes write on my blog. I’ve been long wondering, though, if it is more rational to say shocking stuff to people you know well, or to those you don’t.
I remember this party from ages back where I had just been introduced to this couple, and within ten minutes I’d started expounding the inner beauties of the Goalkeeper Theory (which states that it is okay to hit on someone already in a relationship). I remember the female half of that couple visibly shudder and cling on to her boyfriend within minutes of my exposition.
Some people might recommend higher discretion when you are introduced to someone new, since you don’t want to create a bad first impression. The other way of looking at it is that people you are meeting for the first time, at a cafe or a party or something, are also people you are unlikely to ever encounter once again in life. Consequently, the downside of saying something outrageous is limited. On the other hand, there is a chance that they might be genuinely impressed with your fundaes and you might end up in a stronger relationship (at whatever level) than if you never said the outrageous thing.
On the other hand, while you might be comfortable with people you know well, the danger with saying outrageous or uncomfortable things is that there is a lot at stake. You have already invested significantly in the relationship, which gives you the comfort to say what you want. But if the person genuinely gets offended, you’ve lost a friendship or relationship or more!
So from a risk point of view, if you are the types that likes to make “bold” conversation, and potentially outrage or upset the counterparty, do so when you are still building the relationship. After all, it makes sense to invest in high volatility instruments when the downside is limited!
PS: Don’t try this at a job interview.