Try these 25 conversation starters to hit it off with ANYONE


Never get trapped again in those painfully awkward silences.

  • Picture this: you’re on a first date. You’ve already gone through the routine first date questions (“How are you?”, “Where are you from?”, “What do you do for work?”). Now the conversation has hit a painful lull, and you anxiously look around for the waiter to bring out your orders and break the pressing silence.

  • Everyone’s been there, but with these 25 compelling conversation starters, you don’t have to get caught in the awkwardness again. In fact, you’ll be able to hit it off with anyone.

  • 1. Have you read any books recently that made you see something in a new way?

  • 2. What are your least favorite parts of a first date?

  • 3. If you could go anywhere in this city tonight, where would you go? (Maybe even take them there later).

  • 4. What’s something people wouldn’t guess about you?

  • 5. If you could have any job in the world, what would it be?

  • 6. Who do you trust most? Why?

  • 7. Who was your all time favorite school teacher growing up?

  • 8. Do you have a bucket list?

  • 9. What’s the best show you’ve recently watched?

  • 10. What’s your favorite holiday?

  • 11. If you could only watch three movies for the rest of your life, which three would you pick?

  • 12. If all careers made the same amount of money, which one would you choose?

  • 13. Would you rather have a relaxing Friday evening at home or an exciting one out?

  • 14. When it comes to food, what’s your guilty pleasure?

  • 15. What was the last concert you went to?

  • 16. Where do you fall in your sibling line-up?

  • 17. Have you ever played any sports?

  • 18. As a kid, what did you want to be when you grew up?

  • 19. Do you have any random fears?

  • 20. What’s your favorite kind of food?

  • 21. Tell me the story behind your name.

  • 22. If you could hop on a plane going anywhere tonight, where would you go?

  • 23. Were you ever sent to the principal’s office?

  • 24. What makes you laugh uncontrollably?

  • 25. Did you ever have a movie you watched over and over again as a child?

  • Conversation Tips:

    • Lean more towards playful than serious.

    • Don’t bombard them with questions; let the conversation flow.

    • Answer your own question after they’ve answered – they want to get to know you too!

    • Get to know them, but don’t get too personal or private (“What was your darkest moment in life?”, “Who was the last person you loved?”).

    • Have your listening ears on and try to remember as much as you can. If things go well, you can take the things they told you and turn them into fun future dates or gifts.

    • Don’t be nervous. With the right questions, the conversation won’t get awkward. Plus, confidence is attractive.

  • Some of these conversation starters might sound random or forward, but don’t be hesitant – people love it when others seem genuinely interested in getting to know them better. So don’t let that conversation lull! Instead, hit it off instantly by asking the right questions.

Share with your friends and family…

McKenna Park is a staff writer at FamilyShare. She’s a happy wife, puppy mama, ice cream addict and film nerd. Website:

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