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24 Conversation Starters for the Awkward First Date
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Summary: A great conversation will make or break a first date and can certainly alleviate any awkwardness. But how do you make that happen?

First dates are awkward. There’s no way getting around it even if it’s a date with someone you’ve known forever. Getting over that initial hump where you feel self-conscious you’re not sure what the other person is really thinking can be difficult, especially if you don’t know what to talk about. A great conversation will make or break a first date and can certainly alleviate any awkwardness. But how do you make that happen?


While I don’t recommend bringing a list of questions with you, I would advise you to look over this list and remember a few questions for your next date. If the conversation starts to drift to awkward silence, ask one of these to help loosen the tension and get to know your date a little better.

Where did you grow up?

Where did you go to school/college?

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Do you have any siblings?

Do you have any pets?

Do you play any sports?

What’s your favorite sports team?

How do you like to relax?

What do you usually do on the weekend?

What is your favorite movie and why?

What did you want to be when you were younger?

What are you most proud of?

Are you close to your family?

What are your friends like?

What habit would you most like to break?

Where do you want to travel?

What’s on your bucket list?

Who was your celebrity crush when you were a kid?

What book have you read recently that you’d recommend?

Who do you admire the most?

What’s the first CD/Cassette you ever owned?

What was your first concert?

What’s your greatest fear?

Where are you your happiest?

Have you ever been in love?


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