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What do you talk about on a date? People ask me all the time, “What are GOOD questions to ask on a date?” Rather than boring, same old, same old, questions.

So many of us are in this space of dating where you start to feel like a broken record. Where do you live? Where are you from? What’s your job? and then…What do you say next?!

Once you get all the basic questions out of the way, it can be really difficult to know where to go from there, or what to ask to REALLY get to know someone.

And I don’t know about you, but I’m way burnt out on small talk. The conversation is dull, but you don’t want to overshare, or feel vulnerable…so small talk it is!

Or worse, you get into the questions about relationships…your ex, why it didn’t work out, what you want to be different about your next relationship…not exactly light. Or fun.

Heavy is not the answer. Save heavy conversations for a few dates in, if there’s things that need to be talked about. But first dates (and even second and third dates) are about getting to really know each other. Not the baggage, (because pssst, that’s not actually who you are) but the fun stuff!

What do I mean? Here’s a few questions, in no particular order, to ask to get conversation flowing on a date, where you will ACTUALLY get to know each other at a deeper level, without it all being about your past.

  1. If you had a free weekend, and money wasn’t an issue, what would you do? This gives you a little insight as to what is the most fun for your him/her and what they might like to do with you in the future.
  2. If you could live anywhere, where would you live and why? You get to know a lot about a person, based on the places that are fun for them. And it gives you insight to their political views, landforms they like, or who they might want to live near.
  3. If you had $1000 that you had to give away, who would you give it to? This too, gives you insight as to causes that are important to someone and gives you a peek into their character.
  4. If you were’t in your current career, and there were no barriers keeping you from starting a new one, what would you do instead? This gives you a sense of how happy they currently are in their career, without directly asking, as well as what else is fun for them, as they’ve grown over time.
  5. What was the best thing about the town you grew up in? The worst? This one gives you a little bit of information about their childhood, without being super overt about it.
  6. What’s been the best day of your life so far? This can be a great conversation starter, but use this wisely. If they are divorced, and you think the “best day of their life” might have been their wedding day (or the day their divorce was final), you might shy away from this one.
  7. Five years from now, on this exact day, what do you think you will be/would you like to be doing? This one gives you a little insight into the future…what they hope to accomplish and what they’re looking for regarding a relationship, family, and children…again, without being super “in their face” about it.
  8. Who in your life can you tell absolutely anything to and you know they won’t judge you? This one tells you something about a best friend, close family member, and the people who are most important to them. These are the people whose names you will want to remember.
  9. What do you love to talk about? Some people love to talk about politics, religion, their favorite television shows, etc…Probably a good idea to know if this is something you won’t mind listening to…
  10. What’s your favorite city that you’ve visited? Would you want to live there? Just a great conversation starter. And you may have been to this city too…or you might add it to the list of places you’d like to go.
  11. Where’s your favorite place to spend a day- that you can drive to? Again, this just helps you to know a little bit more about them, and may give you some ideas for future dates.
  12. What hobby do you wish you had more time/money for? People love to talk about their hobbies, what they enjoy, and you get to see them light up. You get to know someone best when you see them talking about things they love.
  13. What’s the biggest misconception people have about you? I love this one, because it helps you to get an idea what other people in their life might think about them, or may also dispel some ideas you might have gotten about them, that may not actually be true.
  14. If you didn’t have to sleep, how would you spend the extra time? This is just another good insight question- Would they write? Watch TV? Draw? Take over the world? You can learn a lot about a person from this.
  15. What makes you feel truly alive? This is where you get a true sense of someone. And also important to look at whether this is something you’d be willing to engage in with this person. Do they LOVE camping, but the idea of sleeping outside sounds like Hell to you? Important information to have.
  16. What event in your life has shaped you the most? Now this gets a little deeper. You might hear something sad here or something inspiring. Either way, you really get to know someone with a question like this.
  17. What’s a really strong opinion that you have? Use with caution, but good to get a sense of politics, things that people are passionate about, etc…to see if they’re in line with your own values.
  18. What do you generally do with your downtime? Do they spend all their time on YouTube, reading, working on their car? This gives you an idea of “a day in the life” should things become more serious.
  19. Life story…Go! This one scares people… but I love it. This is great for a long car ride, long walk, anytime you have time to kill and you want to really learn about someone. People will only tell you what they feel comfortable with you knowing anyways, so don’t worry about this being “too much.”

In general, people love to talk about themselves. There’s been many studies to show that people feel most connected to people that they’ve shared personal information with, more so than those who have been the listener. Obviously, it’s important to ask questions, listen, and share about yourself as well. But keep in mind, that the more time you spend listening, the more connected the other person will feel to you.

Especially, if you are leaning in, asking follow up questions, and being aware that your body language appears engaged.

Let me know if you use some of these and how they work out for you! I’d love to hear other ideas you have as well!

And along the same lines, check out my “How to Write the Perfect Online Dating Profile” PDF HERE!

Love, light, and gratitude,


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