Fun First Date Questions

February 1, 2022

The usual goal with early dates is to get to know new people, people who are different from you. So, if this is your goal, it would seem reasonable that asking great questions and initiating thoughtful conversations would be a good beginning that would allow you to learn as much as you can about each other. These conversations are how you will decide if there is another date in the future. Now, there is no need to put too much pressure on yourself as the first dates are more of a flow of small talk conversation! When you are just meeting someone for the first time you want to refrain from asking way too personal of questions at the start but you also want to get to know that person more than just surface level. Personally, I used to struggle (and still sometimes do) finding a balance between asking those more small talk type of questions while still asking fun and more meaningful conversational questions. It can be a tricky balancing act trying to go with the flow of small talk while also trying to lead to a more beyond the surface level type of convo! So being that we are now more seasoned daters- we have come up with a list for those who may be getting back out there of ideas of questions to get the convo flowing and hopefully lead to fun convo to let you and your dates guard down and hopefully the convo will naturally flow into more meaningful deeper convo.

This list is just a starting point of ideas for first date conversation material! The hope is that these will let you and your date talk about your likes and dislikes and hopefully lead to more fun deeper conversation or at least conversation you can easily discuss! Often time, we have found, that these fun questions lead to a conversation about a topic that either we or our dates can passionately or enthusiastically discuss which brings out another side to you or your dates personality that you don’t see initially with the basic small talk!

Fun Questions To Consider Asking On A First Date: 

  • How long have you been living in X? Where else have you lived? Favorite place you have lived?
  • Where is the next place you want to travel to? If you could go anywhere tomorrow where would it be?
  • Best trip you have ever been on?
  • Did you play sports or play any instruments growing up? What was your favorite?
  • How big is your family? Any siblings?  Are you close to your family?
  • Favorite foods? Food you could not live without? Sweet or salty?
  • Favorite types of books to read? The type of book you’d be most inclined to pick up at the airport?
  • Do you have ant pets at home?  Did you grow up with pets?
  • Where does your family live? Do you visit them often?
  • Favorite types of music to listen to? Favorite concert you’ve been to?
  • What was your latest binge watch material? What genre do you like watching best?
  • Favorite comedy? What is a favorite movie of yours that you feel is underrated?
  • What do you like best about what you are doing now?
  • Are you someone who socializes a lot on the weekends? Are you more extroverted or introverted?
  • Favorite artist? Favorite actress or actor?
  • Do you have a favorite sports team?
  • What was school like for you? Were you the studious type or the type who couldn’t wait to graduate high school/ and or college?
  • Are you close with your friends from high school or the friends you’ve made as an adult?
  • If you could live anywhere, where would it be?

These are just a few questions to get you thinking about things you might want to learn about your dates.  It also helps if there is a lull in the conversation or you’re really into your date and want to get a bit more in depth than the basic conversation. Great questions are always welcome, and show your date that you are genuinely interested in getting to know them on a deeper level.

If you enjoyed this overview of questions to ask on a first date, check out our post on why dating history is a questions we ask on the first date