Rule 7 of 17 · Chapter II — The Conversation
Be interested rather than interesting
Why this rule exists
I must now confess the tactic that undid a lifetime of my finest material: I stopped trying to be impressive. Scandalous, I know. For years I arrived at dates armed with anecdotes, primed to perform, treating each evening as an open-mic set with a captive audience of one. It worked beautifully at making the night about me and terribly at making anyone want a second one. The pivot, the whole secret, was to aim to be interested instead of interesting, to make the other person feel seen rather than to leave them dazzled. People forget your best story by Tuesday, but they remember exactly how they felt sitting across from you, and warmth outlasts wit every single time.
In practice
Drop the mental highlight reel of impressive things to mention and replace it with real attention to the person opposite. When you feel the urge to top their story with a better one, resist, and instead ask them more about theirs. Let yourself be a bit ordinary and unguarded; polished performances keep people at arm's length, while a genuine, slightly imperfect human invites them closer. Laugh at their jokes if they are funny, admit when you do not know something, and let the conversation be a shared thing you are building rather than a stage you are commanding. Being easy to talk to beats being hard to forget.
When it doesn't apply
This does not mean hiding your light or feigning dullness to seem approachable; you are allowed to be witty and to share what you are proud of. The point is balance, offering yourself while staying curious, not erasing yourself to flatter them.