Guides

How to keep a conversation going (without forcing it)

Jonas Berg

Aug 14, 2026 · 7 min read

Four habits that make conversations easier, with questions to try with someone new.

Ask open questions

Questions that start with what, how or when leave room for a real answer. Yes-or-no questions end the conversation for you.

The best next question usually comes from the last answer. Ask what happened next, or how it felt.

A conversation is a trade. Answer your own question too, so it doesn’t feel like an interview.

Start light and only go deeper when the other person does. If answers get shorter, go back to something easier.

Play these as cards

The New Friend deck deals one question at a time and adapts to your answers.

Ask about something they mentioned earlier. People like being remembered.

Say you enjoyed it and name one thing they said. Then go.

Swap the daily debrief for questions that start real conversations, from light to deep.

Questions that give your date room to tell a story, not just list facts.

The stories you never thought to ask about, from their childhood to the day you were born.