20 First Date Questions (Every Person Should Know)

Awkward nervous silence is the killer of a promising first date. Fortunately, I’ve listed some exciting first date exchanges and conversations that will ensure you’ll never have to sit through painful silence and endure boring small talk!

I want to help you break down the barriers and banish both from your dates.

Whether you’re dating at 18 or 88, the key is an easy-going chatty style, attractive questions, while trying to be open-minded and promoting an air of easy communication and understanding. Sounds easy? Actually, it is! 

Just for you, I will lay out my favorite first date questions and start the ball rolling to your second date.

Top Tips: Find Out What It Will Do For Your Dating Life

  • It will help you to gauge quickly if there is a connection, is there a spark?
  • Get a first impression of their personality, find out a bit of background, areas you have common ground. Using these tips makes you one step nearer to finding love!
  • Encourage an open conversation. If they only answer with an abrupt yes or no – collect your stuff and leave! Would you want a date with a robot?
  • Find out if they have any weird hobbies — this information is better known sooner rather than later!

In some of these questions, I have also added a few “don’t ask”  questions. This is because these are the opening lines that are so boring and predictable, you may end up shooting yourself in the foot and waving goodbye to your dream date as he/she disappears through the washroom window.

Some Pointers In Dating

If you have a bad memory you can always take your first date in a coffee shop that puts your name on the side of your cup. The downside to this is when my friend addressed her date as captain sensible for the next seven dates. It’s okay though, they’re married now and she just refers to him as captain! Would you want that?

Chivalry is dead – so sorry to tell you that! Gals and guys, let your date open doors for you but if they stuff their face on your date while you eat salad and then have the audacity to ask you to split the bill 50/50 you are allowed to say, NO, tight arse, then pay for your own and leave, don’t even look back! Even the first date questions can’t help with this problem.

Take heart in the knowledge that even celebrities have problems when dating! A well-known actress aged 62 was blocked from a dating app. No one believed the account was her own, members went on to report the account is fake. Sadly, she didn’t get a chance to try out my first date questions. 

Now reinstated on the app, she is happily dating other fake account holders pretending to be the US president. The moral of the story is everyone deserves to go on at least one first date, no matter who they are pretending to be.

No magic wand here, well, I do! But that’s for my other job, think sparkly leotard! When I am not being cut in half for fun, I like to guide cupid’s arrow into the heart of your lovely daters and give you my favorite first date anecdotes. Pull up a chair people! Let’s begin.

So, What Are The Perfect First Date Questions?

Couple On A Date Server Pouring Wine

1. Hobbies are good for you!

You could say, “Are you working on any spare time projects?” But I would rather go for: “Tell me about the weirdest hobby you’ve ever taken part in.” This is an unusual way of saying what are your hobbies and gives a glimpse into the way a person reacts to being asked about something weird.

First Date Wine Toast

If they immediately go into details and a conversation about collecting toenail clippings, don’t use the cloakroom window, go straight out of the front door and don’t look back!

2. Real-life is interesting!

Another good question to ask when on a date?

“What’s your day-to-day like?” This question is better than, “What do you do between 9 and 5?” But it’s still a bit cringy, so I would go for “Tell me about your day.” Easy, casual, but caring conversation, don’t you think?

This question is about finding things out naturally, while at the same time you will get a sense of what sort of person they are.

3. No worms were harmed in the formulation of this question! 

When was the last time you read a book cover to cover? I love books so someone who doesn’t love books will be put off by this question and wouldn’t be my date. This is a great way to get to the crux of the matter and not a bad thing in my opinion. Equally, if you hate books you won’t want to date a book worm. Life is too short to waste time on worms!

4. More great get to know questions to ask on your first date!

First date questions, personally my favorite thing – “Is there anything you don’t eat?” In my opinion, this might be the most important question you will ask on your date! Food is so important in the language of love, imagine not sharing a fondue in Switzerland or paella in Spain! What if they don’t like Avocado, un-thinkable! 

Eating A Sushi Plate On A Date

5. Followed by the important restaurant question, a must on any first date.

“Tell me about your favorite restaurant!” This question really drills down into the ‘Queso’ and makes it easy to draw out questions and you get to know about their dining habits.

6. Ask about their friends – ‘Tell me about your closest friend or best friend.’

Word to the wise, anyone without friends and I don’t mean the TV show is not datable. This person is not datable, let me repeat that! Not datable. Grab your hat, you’re outta there my friend!

7. “Which animal do you consider more relatable?

Couple With Their Pets

Are you more dog than a cat? A dog person is considered to be more loyal and a cat person more independent. The question is designed to open a compatibility test and is ten times better at getting information out there than “Do you have a pet?” Do think twice if their favorite pet is a snail or a rat, no one likes those creatures unless you’re Dr. Doolittle!

8. Watch out! This one is deep! Deep is good!

What’s the most valuable piece of advice anyone has ever given you?” I love advice and it’s even better if they say “my granny said or my mother said,” that is gold. The answers to this question will give you a deeper look into someone’s soul. More so than ‘don’t eat yellow snow.’ Unless of course, you’re on a date in Aspen. Great advice then!

10. This question is really a second date question but if you make it to dessert, go for it! 

Tell me about how you saw life as a small child? What were you like as a teenager?” This is the point that they tell you something amazing like, “I use to be 20 stone” or “I was really shy.” At this point, you can join in and say something about yourself that may be really important to you, like “I was really shy, too, but now I’m a belly dancer” – You’re not a belly dancer? No? Just me then!

11. Please don’t ask this question! Ever! 

Woman Keep Quiet

Where do you see yourself in five years? This is not a job interview! Mind your own business you nosey person! 

11. Okay, some interview questions will do the trick, I admit to that!

“Tell me about yourself” is a classic interview question and anybody who has been on a job interview would have been asked this question. This my friend, is a trick question! It’s not what they say, it’s how they say it or, more importantly, how long does it take for them to say it? This is relevant to a date situation. Five minutes of ‘I live locally and I work at, blah, blah blah’ – that’s fine. Twenty minutes of how they arrived from birth to now is BORING! Move on!

12. This is like a party game: “or would you rather?” Exciting!

Would you rather eat poison ivy or a handful of bees? Me, I wouldn’t eat either of those. Are you crazy? That should be the logical answer but you rarely get the logical answer, let’s face it, logically is not funny and funny is very attractive.

13. “Would you rather?” Again! I would!

Love this one – “How fast do hotcakes sell?” Hilarious, no? I am beginning to think my sense of humor is a bit odd. In the dating game, you get more information out of someone who is laughing and you’re more likely to want to go on a second date.

14. I feel like we’ve all done this one, for sure.

Woman Worried Holding Her Phone

“Have you ever sent a text to the wrong person?” Yes, I have done that, more than once! This question should open the conversation right up.

15. Good questions to ask on a date – I’m back to my favorite subject, food. 

Is ‘Surf and Turf’ a natural food combination?” Hello! It sure is! The best combination along with mayo on chips, peanut butter and jelly, bacon and maple syrup and deep-fried Mars bars. The last one is a real thing; spend two minutes on the internet with that one. It’s a solid gold food chat! 

16. If music is the food of love, play on!

Couple Man Playing A Guitar

If it’s good enough for Shakespeare, it’s a good enough question for your date. Ask your date about music and bands. If they like Brit-pop, you’re on to a winner, ACDC, not so much!

You can see into the soul of a person when you are discussing music – no musical taste, no soul, no more wasting my time!

17. Karaoke, bring it on! Ask on a first date.

“What is your go-to karaoke song?” Consider the possible choices and what they mean. ‘My Way’ – Frank Sinatra, a traditionalist and in control. As opposed to Avril Lavigne’s ‘Skater Boy’, this shows fun and free-spirit and even more exciting if your date is 88 and still has a skateboard.

18. What’s your DJ name? Funny conversation right there!

Take your middle name and the name of your first pet, add them together and you get some interesting results  – In my case it would be Iris Fluffy! Just exactly what was Fat Boy Slim’s mother doing calling her son Fat Boy? Good job I’m not handing out parenting tips!

19. This next one is a great way to get to know someone.

“What’s the worst joke you have ever heard?” My personal favorite is, ‘What do you call a nose with nobody? Nobody nose!’ Or, ‘What lies at the bottom of the ocean and shakes? A nervous wreck!’ Freestyle on this one, there are so many bad jokes available.

20. Will you call me again?

Woman Shocked

No! Under no circumstances ask this question! You won’t need to ask this question anyway because you have waded through all the last 19 questions and your date has already left. If they are still sitting there you will have an idea of how compatible you two really are. 

One last thing though! – Look down, look at your date’s feet,  brown shoes with black trousers? Don’t date this person unless you want to be interviewed by the fashion police.

Dating style tip number 2: Yellow is no one’s friend. Picasso stated, “yellow is the color of madness!”

Yep, yellow shirt, black trousers, and brown shoes – run for the hills!

Now For A True And Very Personal Story

The question I asked my husband on our first date is not on the list, actually not one of my recommended questions, not now, not then, not ever! Here we go! I asked my husband when meeting him for the first time “Who has died?” Yep! ‘Tell me why you look so miserable and why you look like someone has died'” this is what I really meant.

Reflecting on that now, not sure where my head was at. Was I thinking handsome man but moody? Or sad-looking fellow that might be coming into a shed load of cash inheritance? Heartless you might say! It was neither of those. We had both suffered a loss that year and we bonded over that sadness.  I really miss fluffy!

How Do You Think You Did?

Woman's Face And Question Marks

It’s easy to sit here and think of first date questions or questions to ask when dating, asking those questions is another thing. Think of it as riding a bike! Once you’ve done it a few times you know not to peddle over cobbles!

A good tip is to think about the questions you would like to be asked on a first date. At this point I would like to say, if your date isn’t talking, consider calling 911! On a serious note, if they aren’t asking you any questions, taking time to find out anything about you, something isn’t working. Now! It might be time to end the date. This was their time to shine and if that’s not happening move on, my friend, get the check!


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