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Breaking the Ice.
Ask how they are doing.
How was your day?
What did you do before coming here?
Paying a compliment1 will help put your date in a good mood.
I like your shirt, where'd you get it?
Family and friends.
Ask your date about their family.
What was it like growing up in your family?
Are you close to your family?
Ask your date about their friends.
Tell me about your best friend.
What do you usually do with your friends?
Ask them about their influences.
Who has been the biggest influence on your life?
Food and drinks.
If you are at a restaurant, this is an appropriate time to bring this topic up.
What is your favorite food/drink?
Is there anything that you won't eat?
Do you like to cook?
Hobbies and interests.
Ask your date about what they enjoy doing in their free time or what they're passionate3 about.
What do you like to do outside of work/school?
Do you play any sports?
What do you usually do on a typical weekend?
What things are you really passionate about?
Ask follow up questions on this area, since they enjoy their interests and should also enjoy talking about them.
Entertainment: Movies, TV, Music, and Books.
What was the last movie that you saw?
What type of music do you like to listen to?
Who is your favorite artist?
What do you usually watch on TV?
What is your favorite book?
Career and school.
Ask about what they think about school or their career.
Do you like your job/school?
Ask about what future school/career aspirations4 they have.
Where do you hope to see yourself in 3-5 years?
Current events.
Before going out on your first date, read up on the news, information on the local community, celebrity5 gossip6, sports...
(Try to avoid potentially contentious7 topics such as politics and religion)
Vacation.
Where did you go on your most recent vacation?
What did you do there?
Do you have any future travel plans?
How often do you travel?
If you could travel to anywhere in the world right now, where would you go?
The Past
Reminiscing about the past can be fun and/or nostalgic.
What were you like as a kid?
How have you changed since you were a child?
What is the oddest job you ever had?
Tell me about the first time you broke the law/got in trouble?
Fun Questions
Consider asking some fun questions, such as:
What do people say your best quality is?
If you were granted three wishes, but couldn't use the wishes to wish for money or material goods, what would wish for?
What would you do if you were in a zombie apocalypse?
What would you be doing right now if you weren't here?
What do you hate most about first dates?
What was the last thing to really make you laugh?
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