Our favourite first date questions – ten ideas for better conversation

couple on a first date

A first date can either be an exciting evening where you instantly connect, or an uninspiring encounter which can’t end soon enough. Often the difference boils down to a little preparation; ask the right questions and you could see a totally different side to your date.

To give your evening the best chance of success, here are the 10 first date questions we think may help set the right mood.

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Our 10 favourite first date questions

1. What can I get you?

Whether you’re meeting for a brief afternoon coffee (in fact, the most popular option for a first date among our female members) or going all out with dinner (the male favourite),1 there’s probably going to be a bill to pay at the end. Offer to pay (or at least go Dutch). Why? It’ll not only help your date feel special, but it also displays dependability and kindness on your part. According to recent research, these are near the top of the list of the most attractive personality traits for men and women alike.

2. Dogs or cats?

You: sleeping with your beloved cat Mrs Doyle on a nightly basis. Them: an insufferable cat allergy and they mostly dote on Dougal, their French bulldog. It’s apparent that this might not be a workable partnership – and it’s perhaps best to find out early. This is a great early-doors question, though. It’s equally possible that you’re both dog people and you can already hint at a second date involving your furry friends.

3. Are you an outdoorsy person?

Another one of those first date questions designed to check – subtly – how well your date’s lifestyle might be compatible with yours. Quality time as a couple is wonderful – if you agree on what ‘quality’ time actually is. That’s why it’s not a bad idea to see early on if their idea of a perfect Sunday is binging on a TV series or packing the supplies and heading out to cycle.

4. What tickles you?

In a survey investigating their first date expectations, our members told us that what they really wanted was for their date to make them laugh.2 Asking straight up what makes their sense of humour tick may not get them in stitches immediately, but it’s a simple way to suss out their character and lighten the mood if the date has had a serious tone up until now.

5. Where has been your favourite place to live?

Want to gently suss out someone’s life story without giving them a grilling? Asking about where they’ve lived is a great way to discover if you’re both worldly travellers or if there’s a clash of personalities there. Who knows – you might even hear a wonderful story or two.

Read More: Had a successful first date? Start planning your second date now!

6. What do you love most about your job?

It’s likely that when you first meet, you already know what your date does for a living. Yet talking about our jobs is a classic date go-to when the conversation isn’t yet free-flowing. To give a more interesting twist to the question, ask them specifically what makes them really love their job. This will give you a more interesting answer, lets them really open up about themselves, and hopefully leads the conversation beyond an uninspiring description of their to-do list.

7. What was the scariest moment of your life?

There are few topics more intimate than talking about than moments that get you scared. Sharing tales that you don’t usually reveal is also a great way to understand someone’s character and create a bond between the two of you. Consider sharing your own tale first – and try and keep it cheerful!

8. What’s on your bucket list?

If you’d rather not steer the conversation towards awkward moments past, look to the future and ask your date what’s on their list of things to do before they die. Not only can you then focus the conversation on your genuine passions, but you might just stumble across a mutual love and put the idea in their head to do something together. Second date paragliding anyone?

9. Tell me about your happiest memory

Here’s another one that should help build up the intimacy between you. Not only do questions like this lift the mood and give your date the chance to reveal some closer details about themselves, but giving your date the time to talk will show you’re both interested and a good listener. As Dale Carnegie says in How to Win Friends and Influence People; “To be interesting, be interested”.

10. What are your favourite restaurants?

It may not sound like the most important criteria, but enjoying eating together can be an integral part of a relationship. Finding out where and what they like to eat is an easy way to get to know someone, and it means that if your evening is going well, you can begin to plan your next date somewhere you know will impress.

So – ten first date questions that might help you discover enough about your date to decide if you are a good fit. Naturally these questions aren’t dealbreakers. But, they should combine the right mix of light-heartedness and learning to provide a good image of your date’s character, lifestyle and ambitions – without risking the date becoming an interrogation. What’s best is to trust your instinct; if it feels natural and you’re enjoying each other’s company, you won’t need a script. Nonetheless, it’s good to keep a few questions in your back pocket in case the flow is interrupted.

Ready to give a first date conversation a try? Join EliteSingles today. Happy Dating!

EliteSingles editorial August 2014

Do you have any great ideas for more first date questions? Let us know in the comment box below or email us at [email protected]


1 EliteSingles ‘First Date’ survey, 2013

2 EliteSingles ‘First Date’ survey, 2013


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