Over a Glass of Wine: for the conversation that accidentally went real

There's a question you've been not-asking someone for years. You've decided it's not your place, or there's never a natural opening, or it would make the night weird. So you keep having the other conversation, the one about work and schedules and the kitchen renovation, with a person you'd genuinely love to actually know.

Here's what the research found about that: psychologists had people predict how awkward deep conversations would feel, then had them actually have the conversations. The dread was wrong, consistently. The deep conversations turned out less awkward, more connecting, and more enjoyable than people expected, with strangers and with people they'd known for years. The awkwardness you're avoiding mostly doesn't exist.

These questions go there on purpose. They run light to deep: the hill you'll die on that doesn't matter at all, the thing you're secretly proud of that's never counted anywhere, the best decision you ever made for a terrible reason, who knew you best when you were still the old you, and the one that ends the night, what have you noticed about me. One rule: you ask it, you answer it first. That rule is why the whole thing works.

It fits any table: your oldest friend, someone you met this year, a date, or a whole dinner party going around. If the wine's there, fine. If it's coffee or a long walk, also fine. The conversation is the point.

One evening, any two people or more. Digital download, yours instantly after checkout.

One of the questions inside:
"Who knew you best when you were still the old you?"

Where to go next:

• If tonight earned deeper questions with this person: The Firesides
• For the lighter one, next long drive: For the Road Trip