Ten first date questions: how to make a better connection

Couple in a great first date conversation

So, you have met someone wonderful online. You’ve exchanged a few smiles, a few messages – and now it is time for the big first date. This is always an exciting moment, but when you’re longing to impress, all that pressure can sometimes leave you tongue-tied.

To help you out, EliteSingles has come up with a list of ten first date questions designed to break the ice and get you chatting. Just remember, as well as these ten questions, there are three things you have to keep in mind for a perfect date night. Relax, keep talking – and don’t forget to have fun!

1. Can I get you anything?

A 2007 study by Richard Lippa showed that kindness and dependability are two of the top ten most attractive traits for both men and women.1 With that little fact in mind, a good way to start the date off right can be with a burst of generosity and the first date question we’d all love to hear. Not only will it make your date feel special, you may well come out of it looking pretty attractive!

2. Do you prefer dogs or cats?

Your world revolves around Snickers the chocolate Lab. Cats however? They trigger all your allergies. Meanwhile, your date’s best friend is a moggy called Misty (and neither your date nor Misty get on with dogs). Fundamentally, you two just might be incompatible. If that’s the case it is best to know early, before you get too attached. It goes to show that, sometimes, the more run-of-the-mill questions can be quite enlightening.

3. What’s your favourite thing to cook?

Another way to establish attractiveness is to come across as a good listener.2 To quote Dale Carnegie in How to Win Friends and Influence People, it is a case of ‘’to be interesting, be interested!’’ The best way to pull this off is to steer the conversation towards questions that call for creative, genuinely interesting answers. And of course, you could get the same result from any question that requires your date to tell you a story –but, let’s face it, most people have a signature dish that they are just dying to brag about, right? (and those that don’t may well have some hilarious ‘kitchen disaster’ stories up their sleeves)

4. Are you a summer or a winter person?

This is another first date question designed to see whether you two have harmonious lifestyles. After all, it can lead to a discussion about what you like to do for fun, whether that be skating away the winter, hiking throughout the summer – or even spending all seasons indoors watching Netflix. Essentially, you are trying to establish whether you two could enjoy shared leisure time: a big factor in any relationship.

5. How do you like to relax?

Opening lines and jokes haven’t helped to settle the butterflies? Then why not ask your date about their favourite way to unwind? This isn’t so much about discovering if they are a glass of red person or someone who prefers meditation; it is more about imagining a calming space. Make sure you also share your favourite way to loosen up – research shows that that this sort of recall exercise is not just good date etiquette – it’s actually effective in calming nerves.3

6. What’s your favourite province/city/sports team?

If there is one thing better than travelling, it is enjoying a bit of friendly home-turf rivalry. If your date seems like they might be up for the challenge, then why not employ an old playground tactic and indulge in a bit of flirting by way of gentle teasing? Are they an Oilers fan? Then talk up the merits of the Flames! They’re from Ottawa? Then mention your Montreal connections. The main thing to remember is that, for this to really pay off, you have to keep it light-hearted. As flirting coach Kimberly Seltzer advocates, this type of talk should always be “fun and playful.”5

7. What’s been your favourite travel destination?

Want to find out a bit more about your date’s life without it seeming like an interrogation? Then try this classic first date question. It can give you insight into a person’s background while also letting you hear an interesting story or two. After all, this is a nation of travellers4 – so chances are your date will have some pretty fascinating stuff up their sleeve!

8. What’s the funniest thing you’ve seen recently?

If this sort of flirting sounds a little too risky, then why not play it safe and put your efforts into making your date smile? In our 2013 EliteSingles members’ survey, the number one first date hope, for both men and women, was that their partner would make them laugh.6 The easiest way to do this? Get them to tell you a funny story so you can get to know their sense of humour.

9. Tell me about your happiest memory.

Sharing happy memories with your date is a great way to bond. In part this is because the sharing itself can create even more warm feelings. In fact, a University of Southampton study found that remembering happy memories can actually promote optimism and create a positive outlook.6 In other words, it creates pretty perfect date conditions.

10. Do you want to see me again?

This may very well be the ultimate first date question. But before you ask it, you need to ask yourself a question: am I having fun? After all, that is what all the above questions are about – building a mutual, easy rapport that may eventually lead somewhere wonderful. If you are feeling all of that? Then it is time to ask for that second date.

Are you ready to start a conversation with a like-minded, local single? Then join EliteSingles today!

EliteSingles editorial, August 2014.

Do you know any great first date questions that we might have missed? Let us know below or email us at [email protected]


1 Lippa, R. A. (2007). ‘The Preferred Traits of Mates in a Cross-National Study of Heterosexual and Homosexual Men and Women: An Examination of Biological and Cultural Influences’. Archives of Sexual Behaviour, Vol. 36, 2, pp192-208
2 Susan Heitler, Ph.D, writing for Psychology Today, The Art of Listening: How Open Are Your Ears?
3 Vesta Giles, writing for Canadian Living, 28 tips to help you relax instantly.
4 Canada.com: Travel rebounds as savvy Canadians look for new experiences. From Postmedia news.
5 2013 EliteSingles interview with Kimberly Seltzer, flirting coach and head of EliteImageMakeovers.
6 EliteSingles ‘First Date’ survey, 2013


About the author: Sophie Watson

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