Fun First Date Questions

First Date Questions to Kick-Start a Great Conversation!

9/23/2020

One of the most-nerve wracking parts of a first date is keeping the conversation flowing and avoiding those awkward silences! Here’s our favorite conversation-starting questions that will help kick-start an interesting and fun conversation, while also helping you really get to know that person across from you in a thoughtful way. Keep these questions in your back-pocket to spark that connection!

What is one thing I might not guess about you?

This is a simple and light-hearted question that helps you learn something about your date that you may not have stumbled across otherwise. First-impressions can often be deceiving and this gives you both an opportunity to put those pre-conceived notions to rest. It is also a bit flirty and fun while simultaneously showing your date that you want to get to know them on a deeper, less-surface level.

What are 3 things you would like to accomplish in your lifetime?

Not only do you want to learn about their past and present, you also want to know what dreams they may have in their future (so you can begin to figure out if you want to be apart of it!). This question lets you learn about your date’s goals and plans which will help you get to know them while also allowing you to see if those plans are compatible with your own!

What do you like most about living here?

Where you live is likely something you two already have in common, so it is a great way to kick off a conversation because you are already familiar with the topic! You can also learn so much about your date’s preferences and interests (and, if the date goes well, it could help you come up with second date ideas they would enjoy!).

If you no longer needed to work and money was not a factor, what would you spend your time doing?

This is a fun and unique question that will help you figure out what kinds of activities and pursuits your date is interested in. The answers to this question will help reveal some more personal dreams and desires, while not seeming too intimate for a first date.

What are you MOST passionate about?

This is a great conversation starter because you know that their answer will be about something that they are incredibly interested in. It is easy to ask follow up questions about their passion because it is a topic that most people would love to talk about!