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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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Questions to Ask a Girl

For a date, a text thread, or getting past the version everyone gets.

1. What's something you're into that surprises people?
2. What's gone right this week?
3. What did you spend all your time on as a teenager?
4. What's your comfort film or show?
5. What are you working on in your life right now?
6. What kind of people do you end up close to?
7. What's something you've had to learn the hard way?
8. What makes you walk into a room differently?
9. What did childhood hand you that you're still holding?
10. When were you most on your own?
11. What are you afraid people would see if they looked closely?
12. What's stayed entirely yours, never spoken?

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Questions to Ask a Guy

For a date, a text thread, or a friendship you want to move past small talk.

1. What's something you're good at that never comes up?
2. What did you want to be at eleven years old?
3. What's the last thing you got properly into?
4. Two days, nothing owed to anyone — what happens?
5. What are you actually working towards?
6. What's something you've changed your mind about?
7. Who taught you the most about being a man, and what did they get wrong?
8. What do you do when things go badly?
9. When did isolation hit you hardest?
10. What do you never talk about?
11. What version of yourself would you hate to meet at fifty?
12. What have you never forgiven yourself for?

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Questions for Your Crush

From safe enough to send at 4pm to the one that changes what you are.

1. What's the best part of your day usually?
2. What are you avoiding doing right now?
3. What's something you'd do every weekend if you could?
4. What's your most-used app that isn't messages?
5. What do you notice first about someone?
6. What's the fastest way to get your attention?
7. What do you find attractive that isn't about looks?
8. When did you last properly fancy someone?
9. Have you thought about me when I wasn't around?
10. What have you been wanting to say and haven't?
11. What would you do if I said I liked you?
12. What's stopping you?

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