One of the best ways to get to know someone quickly is to get them to talk about themselves! By telling your date about some personal non-TMI stuff during the first date, you are essentially letting them get to know you better at a rapid rate as opposed to just letting the getting-to-know-you stage play at its own pace. By asking fun first date questions immediately, you are essentially hacking your love life and telling them about yourself. When a person finds out something personal about you, they will be able to sympathize or empathize with you and this helps build the relationship. 

couple on first date, fun first date questions to ask

Don’t be afraid to get in there with fun first date questions – it shows them the cheeky side of you that’s really interested and lets you get to know them on a different level so you can see if there’s a connection. Try to avoid getting too TMI or personal – you don’t want to make them feel uncomfortable. The questions you ask should be based on things that will show you what type of person you’re dealing with and a good way to gauge how they react to certain topics and how they express themselves—either honestly or with reservations. No matter what they say though, the very act of sharing will definitely help you grow closer. 

These are some of my fave questions to ask during a first date – ask open-ended questions to keep the conversation going!

Fun first date questions to ask

  • Where did you grow up? What was your family like?
  • Who do you admire the most right now?
  • If you had a free plane ticket to anywhere in the world, where would you like to go?
  • Aside from your current job, what’s something you would love to try? What’s your dream job?
  • What’s the best part of your daily routine?
  • What was your most embarrassing moment? 
  • What’s your biggest fear?
  • What’s your number one pet peeve?
  • What little thing makes you extremely happy?
  • What do you love about this city?
  • If someone gave you a blank check, how much would you write it for and what would you spend it on first? 
  • What movies have made you cry or laugh the most?
  • Where would you like to live for the rest of your life?
  • How do you start your day?
  • Are you a dog or a cat person?

Of course, when you’re getting into personal questions, there are some topics that are a bit too TMI or personal. These are the things you’re going to want to avoid talking about on a first date:

  • Bodily fluids. Save that for when you start getting intimate. You don’t want to cross the line or turn them off!
  • A death in the family. Let them express themselves about this on their own time.
  • A mental disorder or illness. Don’t probe – if they’re going through something, they’ll tell you when they’re ready.
  • Salaries – this one is just tacky! Finances are something you can discuss when you’ve gotten to know each other better.
  • Past relationships. There’s no way to send them running for the hills faster than by digging into breakups or the one that got away!

Need more help getting ready for that first date? Check out our date coaching options!