Ask an open-ended question about something specific they mentioned
Give a brief, genuine compliment related to something they said or did
Share a relevant personal detail and ask for their perspective
Comment on a current event or shared context, then ask what they think
Start with a low-stakes question (plans, interests, recommendations)
Ask for advice (“What would you recommend for…?”)
Invite them to talk about their work or project (“How did you get into…?”)
Reference a common connection (mutual friend, group, event) and ask a follow-up
Use “What’s something you’ve been into lately?”
Offer a simple choice question (“Are you more into X or Y?”)
Start with a light observation about the situation (“This is a busy place—how’s your day going?”)
If texting, respond to their last message with one question and one related comment
Mirror their tone and energy level
Keep the first message short and easy to answer
End with a clear question to make replying effortless
If they respond briefly, ask a narrower question
If they seem engaged, ask one follow-up question and share a related point
If the topic stalls, pivot to something else and ask another open question