The awkward lack of discussion on dates happens even to the most seasoned of couples. Don’t feel insecure if it’s happening on your first date! There’s only so many things you can say, and sometimes nerves keep even those from coming to mind. Luckily we’ve discovered 16 interesting conversation starters to keep your dialogue going. Try memorizing a couple and keeping them in your back pocket… You never know when you’re going to need one!

1. What are you reading/watching right now?

A nice neutral topic, this gets the conversation focused on their likes/dislikes. Be sure to follow this up with “Would you recommend it?” to get more of their opinion.

2. What’s your favourite meal?

Keep this in mind for future reference. If you’ve gone for coffee as your first date and they say they like pasta, suggest the Italian place down the street for your second date. It shows you’ve listened, and taken to heart what they’ve said.

3. Describe your perfect day.

Another cute way to subtly get date ideas. Try to get them to go into detail, and imagine it as clearly as possible.

4. What’s your least favourite word?

A fun question, especially if your date likes language.

5. Can you speak any other languages?

Maybe you two are fluent in multiple languages, or have a desire to learn more languages. You could find yourself a new conversation buddy!

6. In grade school were you better at math, or language arts?

This is a fun one to figure out what type of thinker they are. Are they more numerical? Strategic? Maybe they’re more creative? Who knows what you’ll discover!

7. Are you allergic to anything?

A basic question. This is important information to know about any partner.

8. What’s your quirkiest habit?

This question is very cute! It also offers an insight into their self-reflection. How do they see themselves? Is it different from how you’ve seen them so far?

9. Do you like what you see when you look in the mirror? Would you change anything?

Some people might take offense to this question. Only ask if you’ve gotten far enough along in the date to trust each other with such a private topic.

10. Do you consider yourself a “quick learner”? How has that helped or hindered you in life?

These sorts of discussion questions will get you far in the relationship. Staying focused on your partner will flatter them, and they’ll be more inclined to open up and trust you.

11. What’s the wildest thing you’ve ever done?

This question can get you some very, very interesting stories… Ask only if you’re feeling brave!

12. Do you find it easy to say “no” to people?

Don’t over-think their answer. Know that they’ve agreed to date you because they like you, even if they do have trouble saying no.

13. Is there a current music/fashion trend you really hate?

It’s always fun to make fun of the current trends. This can infuse some humour and energy into your discussion, and revive a dying date!

14. Where have you traveled?

If they haven’t gone anywhere then a good follow up is “Where would you like to travel?”

15. If you could change one thing in your life, what would it be?

It doesn’t have to be negative. Prompt them with ideas like skills they wish they’d picked up sooner, or something in their youth they wish they’d experienced.

16. What do you think about ______?

When you get right down to it, asking someone what they think of anything is a great conversation starter. People love to talk about their ideas and opinions… You might even get into a friendly debate!

Let us know what you think of these! You can email us at

16 Questions To Ask on a First Date