Say It First All guides

Dating & social

How to keep a first-date conversation going

You’re talking to Jamie, your date. The goal: ask good questions and share a little about you.

Your first line

Jamie starts with “So... this place is cute. Have you been here before?”

“Never, it’s my first time too. I picked it for the patio. Do you have a go-to spot around here?”

Share back, then ask: answer their question with a small real detail, then hand it back. It feels like a conversation, not an interview.

What Jamie might say, and what to say back

  1. Jamie: “Oh, work’s fine. Nothing exciting.”

    You: “Fine is fair. What’s the best part of it, though? There’s always one.”

  2. Jamie: “Not much, honestly. Work, sleep, repeat.”

    You: “Ha, same lately. If you had a free Saturday with zero plans, what would you do?”

  3. Jamie: “Ha, um, I don’t know.”

    You: “That’s fair, that was a big one. Okay, easier: best thing you’ve eaten this month?”

Two things that trip people up

Now say it out loud

Reading the words isn’t the same as saying them. Practice this one with Jamie pushing back like the real person would. Then your coach, Sol, fixes your exact words. The move to focus on: Share back.

Practice this one free

3 free reps a day. No sign-up. Out loud or typed.

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