First Date Questions — Free Conversation Starters Online

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First Date Conversation Starters

Openers for the first ten minutes, when neither of you has settled yet.

1. How was getting here — did anything go wrong?
2. Have you been here before, or are we both guessing?
3. What's been the best part of your week?
4. Are you a nervous-talker or a nervous-quiet person?
5. What made you want to meet up?
6. What do you actually enjoy about what you do?
7. What's something you've got better at recently?
8. What kind of people do you gravitate towards?
9. What are you actually hoping to find?
10. What's the hardest thing you've been through recently?
11. What have your last relationships taught you?
12. What do you know you do wrong in relationships?

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First Date Questions

Questions that tell you who someone is without making it feel like an interview.

1. What's been the highlight of your week?
2. Are you a planner or do you figure it out when you get there?
3. What's something you're into that most people find strange?
4. What did you do before this that you thought you'd do forever?
5. What made you say yes to this?
6. What's something you're working on about yourself?
7. What kind of people do you end up closest to?
8. What's a decision that changed the direction of your life?
9. What are you actually looking for — and are you telling the truth?
10. What's the pattern you keep repeating in relationships?
11. What's something you'd want a partner to know early?
12. What's the loneliest period of your life been like?

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Getting to Know You

For dates two through five, new friends, and anyone you're still figuring out.

1. What's your ideal way to spend a day off?
2. Are you an early riser or does the morning happen to you?
3. What's your most-used app and what does that say?
4. What's a subject you could talk about endlessly?
5. What's shaped you most that isn't obvious?
6. What do you need to feel comfortable around someone?
7. How do you handle conflict?
8. What do you do when you're overwhelmed?
9. What's the thing about you that takes people longest to understand?
10. What are you most insecure about?
11. What's a wound you're still carrying?
12. What do you need that you've never been given?

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Three levels deep