escort diary® of Jolie: On being asked the right questions
Most of the questions people ask each other are not really questions but are conversational placeholders: small pebbles you toss into the silence so that neither of you has to sit in it.
How was your weekend.
What do you do.
Where are you from.
These are not questions.
I am not against them, they have their place and I will use them at times. You cannot open every conversation with what is the thing you're most afraid of admitting, or you would have no friends and possibly a restraining order. The handshakes exist for a reason: they give two strangers a way to verify that they are both, in fact, willing to participate in the thing called a conversation before either of them risks anything.
But the handshakes are not where the evening lives.
The evening lives in the second questionm the one that comes after you've answered what do you do and the other person actually pauses, looks at you, and asks something that proves they were listening.
I have a theory that most people go years between being asked a question they actually want to answer. Not because the people in their lives don't care, they often do, but because nobody was taught how to ask the second question. We were taught how to make polite noise. We were taught how to fill the silence, we were not taught how to follow up, which is the one skill that turns small talk into something worth remembering.
So this is what I do, when you sit across from me. I ask the second questionand the third and the fourth and many more. Not because I am performing curiosity but because I am, embarrassingly, actually curious. I want to know what you meant when you said that, what you didn't say, why you paused before answering, and what was in the pause.
Most people are not used to this, which I can usually tell within the first few exchanges. There is a particular look that crosses someone's face when they realise the question I just asked is not a placeholder: that I am waiting for a real answer, that I am willing to sit with whatever comes out.
It is somewhere between surprise and relief... and sometimes it tips into something more vulnerable, and they have to look away for a second to recover.
What I have learned, doing this for years, is that the best evenings are not the ones with the best stories or the wittiest banter or the most charged chemistry. The best evenings are the ones where, somewhere in the middle, someone realises they have been talking for a while, actually talking, not performing, and they did not notice it happening.
This is the moment the evening became itself.
You cannot manufacture this and you cannot turn it on by asking the right question at the right time, because the magic isn't in the question, it's in the willingness to actually want the answer. People can always feel the difference.
The question that wants a real answer arrives in the room with a different weight than the question that wants a polite one, and the body responds to it before the mind has even decoded the words.
I think about this a lot. I think about how rare it is, in most people's daily lives, to have someone look at them and ask something that says I see you, and I'm interested in what's actually inside you, not the version you bring to dinner parties. I think about how much loneliness exists not because people are alone but because they are surrounded by handshakes and starving for the second question.
That is, in some ways, what I offer. Not the only thing, and not the most obvious thing, but possibly the thing that lasts longest after the evening ends. The feeling of being asked something real, by someone who actually wanted the answer, in a room where there was no agenda and no audience and no reason to perform.
It is a small gift for both of us, and it is, somehow, one of the rarest things in the world.
If you come and see me, you will be asked questions (a lot). You may, depending on how the evening unfolds, be asked something you have not been asked in a decade.
You can answer however you want. You can tell me the truth or you can tell me a story or you can change the subject entirely, I am not here to extract anything from you. But the question will be there, and it will be real, and you will know the difference.
And if you have been walking around for a long time wondering why every conversation you have feels slightly hollow at the centre, this might be why.
Not because the people in your life don't care, but because nobody has been taught how to ask the question that lets you put down whatever you've been carrying.
I'll ask, since I'm pathologically interested.
