7 Conversation Starters that Aren’t a Buzz Kill

Have you ever experienced those awkward silences on a first date? Where the energy fizzles and dies, and you’re not quite sure how to get the conversation back on track?

You’ve already covered the obvious bases. Dating history. Check. Hobbies. Check. Favourite Netflix series. Check.

Now what?

It’s not easy to think of great questions on your feet, especially when first-date jitters get in the way. So, I’ve compiled a small arsenal of questions (some stolen or adapted from interviews I’ve read in various publications) to help you spice up the chatter and get to know your date better.

Drum roll…

What are 10 things you can’t live without?

Toronto Life used to have a series called “The List”. Local celebrities listed ten things they couldn’t possibly live without. There’s some whimsical items on these lists like a 100-year-old egg timer that a chef inherited from his grandma. This question is an indirect way of discovering someone’s hidden treasures and background!


If you were having a party and could invite any famous Canadian (dead or alive) who would it be?

Who someone admires tells us a lot about their own character. And, it’s a good sign if your date is fascinated by people who fascinate you too. Wouldn’t it be cool if they said they would invite Drake, and you are a huge fan? But even if they say they would invite Justin Bieber and you are not a “Belieber” that would still spark an interesting conversation!


What reading material is now on your nightstand?

There are many signs that tell us whether a first date should lead to a second date. Physical chemistry, of course. But what about intellectual sparks as well? Asking your date what they are reading, will give you more insights into their passions and curiosity.


If heaven exists, what would you like to hear God say when you arrive at the pearly gates?

James Lipton, former dean of the Actors Studio Drama School interviewed actors on his show Inside the Actor’s Studio. This was one of his famous questions. It’s a great date question too, isn’t it? Wouldn’t you want to know the kind of legacy your date hopes to leave or even the skeletons in their closet they want God to forgive?


What profession other than your own would you like to attempt? 

This is another question that James Lipton asks that I think works well on a first date. Many of us had childhood dreams—an actor, a race car driver, an Olympic figure skater. What is your date’s secret ambition, and why? Do they have any plans to reinvent themselves?


If you found a winning $10 million lottery ticket on the sidewalk after our date, what would you do?

I saw a similar question on Quora and it got me thinking about what answers reveal about a person. Would your date use the money to start a charity to help people in need; buy themselves a fleet of Porsches in every colour; try to find the rightful owner of the ticket? What kind of answer could make you fall in love?


How would you spend a perfect Saturday?

This is another question Toronto Life used to ask local celebrities. It’s a great thought experiment for a first date too. If your “perfect” Saturday is to rise early and go for a long bike ride, it might be a drag if your date’s perfect Saturday is sleeping in till noon! On the other hand, if their perfect day looks a lot like your perfect day, this might be the start of something fun!


Getting to know someone new is a whole lot easier when you have interesting things to talk about. Having a few good questions up your sleeve will help you in your discovery process and provide some laughs along the way!