What to actually say
Open with this, more or less word for word: We've officially run out of small talk, which honestly might be the more interesting part of the night.
We've officially run out of small talk, which honestly might be the more interesting part of the night.
Naming the silence out loud takes its power away; it stops being the elephant and becomes a joke you're both in on.
What's something you used to be sure about that you're not sure about anymore?
It has enough texture that a one-word answer is actually hard to give, and it invites a real thought instead of a resume line.
You mentioned your sister earlier — are you close, or is that a complicated one?
Going back to something they already said proves you were listening, which does more for the evening than any new question could.
I'm going to admit I had three more questions lined up and I'm retiring all of them.
Self-deprecating honesty about your own prep gives permission for the date to stop performing too.
How it usually goes
A version of the conversation with the push-back left in, because that is the part you need to have already heard once.
What not to say
So, tell me about yourself.
It hands them an entire autobiography to write on the spot, which is exactly the kind of open-ended pressure that kills momentum.
Awkward silence, huh?
It labels the discomfort without giving either of you anything to do with it, so it just sits there twice as loud.
Do you come here often?
It signals you've stopped trying, and most people can feel a script being read at them.
If they answer everything in three words or less
This is the moment people panic and start asking more questions faster, which makes it worse — you start to feel like you're interviewing someone who doesn't want the job. Stop and check instead of guessing. Say: 'You have real short answers tonight — are you generally quiet, or is this just not landing for you?' It's direct without being an accusation, and it gives them room to say 'long day' instead of making something up. Whatever they say, believe the first answer. You don't need to fix a bad match, you need information.
