Great First Date Questions - Stoic Matchmaker

10 Great First Date Questions

10 Great First Date Questions

January 19, 2022

A first date is a great opportunity to find out more about someone. Besides picking a great place to go or fun activity to do, you’ve got to be able to have a good conversation with the person you’re meeting. 

The last thing you want is awkward silences and staring off into space, watching the minutes tick by without meaningful conversation. No date needs to happen like that. 

To have a great conversation, you need a starting point, a launching pad if you will, that will lead to other topics and discoveries along the way. 

Here are 10 great first-date questions to help you discover more about that mysterious person you’re seeing.

  1. What do you like to do in your free time?

Nothing gets someone to open up like talking about themselves, especially their hobbies or interests. This can help break the ice. 

  1. Are you more of an introvert or extrovert?

Although you may discover this without asking the question, posing this question can give you insight into why they may be one or the other. 

  1. What’s something you’d like to learn or be better at?

This question can help you see and understand your date’s aspirations in an area of their life, some of the things they value, or activities where they want to improve.

  1. What TV series or movies do you find yourself returning to and rewatching?

This one may help you discover common bonds in film and TV. You may even want to share your own list.

  1. Who is your best friend and why? 

Most people have a best friend they rely on. Some interesting follow-up questions might be: How did you two meet? How long have you been friends? How often do you get to see them?

  1. Among all of your friends, what are you best known for?

You could even treat this as a game by filing the answer away and asking the same question later to their friends when you meet them. 

  1. Do you have any projects that you’re working on that you’re passionate about?

This could even turn into a life goal type of conversation and can give you insight into where they want to go in their career or life. 

To keep the conversation light-hearted, you might even throw in a couple of the following questions. 

  1. Have you ever attempted telepathic communication with your dog?

Yeah, cheezy, but you can still get information with this one. Your date will most likely be quick to say they don’t like dogs or prefer other pets Or who knows, maybe they are the next Dog Whisperer. 

  1. What is your favorite vacation spot and why?

This can open up a whole avenue of conversation about travel.

  1. What’s your favorite type of food?

Another good one because you’ll probably be spending time eating at some point during your date. 

And there you have it! Ten great first-date questions to kickstart the conversation and learn more about each other. Prepare yourself and go out there to have some fun!

Remember: “It’s the Situation Keeping My Connection with Him”.

I’m Lori Stith, The Stoicess, and I believe in You!

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