20 Best First Date Questions to Ask a Guy

By on October 7, 2013

Ladies, the typical first date questions are boring. Where do you work? What do you do in your free time? Do you hope to have a family someday? You might want to know the answers to these, but they are boring, cliché, awkward and will not get you a call back. Try these 20 questions for a more fun and memorable first date.



Most embarrassing moment 

Why you should ask;

This question immediately lightens the mood and makes both parties at ease more. Plus it will probably provide for laughs and a window into better stories.


Pet Peeves

 Why you should ask;

Ask this one immediately in case your date’s pet peeve is women paying or something else you planned on doing.


Person you would most like to have dinner with

Why you should ask;

This question says a lot about a person without asking a million boring questions. Plus, it makes me think since they weren’t anticipating answering much beyond where they worked.



 Why you should ask;

Every tattoo has a story and a reason. Some tattoos have hilarious stories and some have sentimental value. Either way, they too say a lot about a person.


Dream vacation         

Why you should ask;

Where a person wants to go in their free time can tell you a lot about them. If they would go to China, they might be more cultural. Greece is more historical. The Alps is more of an outdoorsman. You get the idea.


Dream job   

Why you should ask;

This is a good question that will lead to where they really work without you asking such a cliché question. Also you get to know if they are doing what they are passionate about or not.


Favorite dessert

Why you should ask;

This question has no hidden deeper meaning, but it lightens the mood and maybe you can share one if you have a common favorite.


What would you do if you won the lottery?

 Why you should ask;

Would they donate a lot to charity or spend it sole on themselves? This offers a bit into their soul. If they are shallow and materialistic, it will show really quickly. If they mention paying off bills, it shows financial responsibility.


Where do relax the best?

Why you should ask;

This questions helps tell if your date is high-strung or not. If they can relax anywhere, that is great. If they cannot relax anywhere, that is bad.


Weirdest dream

Why you should ask;

Another “for fun” question that is guaranteed to bring laughs, especially if he reveals that he once had a dream about living with the Smurfs.


Toilet paper roll under or over

 Why you should ask;

No one asks this question on a first date. Your date will remember you for sure. And everyone has a preference.


 Ever been skydiving, bungee jumping, etc?      

 Why you should ask;

This answer will tell if he is into thrill sports or more reserved. Does he take chances or play it safe? Which type of guy do you prefer?


Favorite comedian    

Why you should ask;

A person’s type of humor reveals a lot about them. Does he enjoy raunchy humor or safe humor?



Why you should ask;

This will probably lead to another great story and you will know a more private detail about him. If he shares his with you, share yours with him as well.


What did you do on your 21st birthday

Why you should ask;

It will guaranteed be a great story. Then you can share yours as well for maximum laughter.


What were you like in high school?      

Why you should ask;

This question will tell a lot about who he is now. Sure people change, but do they change that much? That conceited football star might be similar to the man he is now.



Why you should ask;

Guys love to tell about their battle wounds. No matter the story, he will probably exaggerate and make himself a hero out of it. It’s good entertainment.


How many places have you been to?  

Why you should ask;

The more traveled someone is, the better they are at looking at the big picture. Someone who has barely made it outside their hometown city limits sign has a very narrow view of the world.


Morning or night person?

Why you should ask;

No one wants to date the morning people. Unless you are one too.


Do you collect anything?

Why you should ask;

This question offers a little insight into them without asking a million other questions. Also, it opens up the ability to see if you share some interests.


Leave a Reply

Your email address will not be published. Required fields are marked *