First message
Question
What’s something you could talk about for hours?
Follow-up: What got you interested in it?
Question
What’s your idea of a really good first date?
Follow-up: What would make it feel relaxed?
Question
Do you prefer a thoughtful message or a spontaneous hello?
Follow-up: What makes a message feel personal to you?
First video chat
Question
If we could swap places for an afternoon, what would you show me?
Follow-up: Where would we go first?
Question
What song would you put on for a good conversation?
Follow-up: Is there a story behind that choice?
Question
Are you usually the one making people laugh?
Follow-up: What kind of humor gets you every time?
Getting comfortable
Question
What’s a small gesture you find surprisingly charming?
Follow-up: Has anyone done that for you recently?
Question
Would you choose a planned date or a spontaneous adventure?
Follow-up: What would your version look like?
Question
What’s a compliment you still remember?
Follow-up: What made that one stand out?
Shared interests
Question
What would you teach me if we had an hour together?
Follow-up: What would be the first lesson?
Question
Is there a place you’d love to show someone?
Follow-up: What makes it special to you?
Question
What would make you want to keep talking after a first chat?
Follow-up: What usually tells you that you’re comfortable with someone?
Follow Her Answer, Not the List
If you ask what she could talk about for hours and she says music, ask which artist she has returned to lately. If she mentions a concert, ask what made it memorable. The useful follow-up comes from her answer, not from the next number on this page.
When to Change the Subject
If the reply is brief, she does not respond, or she says she is uncomfortable, move to an easier topic or end the conversation. A playful question should invite a response, never pressure someone into one.