First dates are pretty nerve-wracking no matter what you’re normally like. You’re putting yourself out there to be judged by someone you probably don’t know very well, and odds are you already think they’re nice. Ruining things with flat chat is crushing.
For me this has gotten better over the years for sure. With a bit of time, a bit of practice, and some solid advice. Some of that advice is to come prepared!
So, what are good questions to ask on a first date?
Unless your date has been planned extremely spontaneously, you’ve definitely got time to think up some fun and interesting conversation topics for when that awkward silence hits, and today I’m going to run you through 20 first date questions that for me have resulted in laughs, deep chats and most importantly, second dates.
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1. If you could travel anywhere tomorrow, where would you go?
If a passion for travel is something you and your date share, this one is particularly good. It can be fun and lighthearted, exchanging silly stories and language mix-ups from past holidays. It can go a bit deeper since a lot of people have had pretty big or life-changing experiences on their travels.
You can discuss the best dishes you’ve eaten, the most beautiful sights you’ve seen, and the best friends you made along the way. You can share your dream destinations and see if any of them match, planting seeds for future adventures…
2. What’s the best meal you’ve ever eaten?
You know what they say, the fastest way to a man’s heart is through his stomach. Ditching the outdated gender roles implied in that phrase, I think the sentiment applies to most people. Food is important!
Your date might tell you about the lavish Michelin star dinner they had on a special occasion, they might tell you about a surprisingly delicious street food dish they had abroad, or they could talk about their mother’s cooking that they think is the absolute best.
There are plenty of options since food has a really special place in most people’s lives, so it’s a great conversation topic for a first date. This question will get much better and longer answers than ‘what’s your favorite food?’
3. If you won a million dollars tomorrow, what would you do?
A fun one! Man, I love to dream about what I would do with a million dollars. And I bet your date will too. Money is such a drag, imagining a life where money is no object is the ultimate fantasy.
Remember to sprinkle in some altruistic options to make you seem like a good person. Donating to charities, building schools for the disadvantaged, you know, that kind of thing.
Not that you aren’t a good person, I’m sure you are. I bet those things are already in your fantasy!
No doubt your date has thought about this in the past too, and you can have some fun building your imaginary lives.
4. Did you have any nicknames when you were a kid? What about now?
Nicknames can be a sore point for some people, we all know that. Nicknames from childhood can be embarrassing, given by bullies or older siblings for things we weren’t super proud of. I’m choosing not to disclose mine here on the internet for everyone to see.
But most of them are at least funny in hindsight and can be the source of a good laugh, and a little bit of an ‘I’ll tell you mine if you tell me yours’ situation which is always fun on a date. Nicknames given in adulthood usually have a pretty funny or weird backstory, too, so worth asking.
5. What’s something I wouldn’t guess about you?
You guys have only just met so there are probably loads of answers to this question. It can be quite revealing, what does your date think is surprising about them? What do you think is surprising about you? Mine is that I’ve seen Take That live in concert 5 times, which I can tell you is genuinely surprising to most people. What can I say? They’re iconic.
Whether your date has 10 cats or is a world champion lawn bowler, you’re bound to get some good conversation going from asking a question like this, as well as an opportunity to make them laugh with some shocking information about you.
Side note, this isn’t the time to reveal any horrific crimes you’ve committed.
6. What’s on your bucket list?
This is a classic. Some might think it’s a cheesy question but come on, it’s a surefire way to learn about someone’s wildest dreams, so why wouldn’t you ask it? People’s bucket lists can be really out there, or pretty tame.
According to USA Today ‘fall in love’ is at the top of 83% of singles bucket lists. That’s something you could help with! Also up there are wine tours of Napa, swimming with turtles, and seeing the northern lights. Less common answers are enrolling in survival classes and space travel. These answers will tell you a lot about your date and the life you could lead together.
7. What’s been the most significant or best year of your life so far?
This is a deep first date question, so only ask it if you feel like you want to know your date on a deeper level.
Not everyone has a huge pivotal year that was really significant, but some people do. Even if it wasn’t anything crazy, most people could choose a year of their lives that had a big impact on them or changed their perspective.
This question will encourage honesty and reflection, and whatever the answer it will probably invoke some long responses and deep conversation, or let you and your date talk about some great times.
8. What’s your family like? Tell me about them.
Our families shape us and are the people who usually have the biggest impact on who we are as people. Whether they have a good relationship with their family or a complicated one, people can normally talk about their family forever so this is a good question for avoiding awkward silences.
It will also bring you closer to your date since it’s such a personal topic, and most people have some pretty wacky family stories. Keep in mind that some people might not want to talk about family stuff, and if you sense that, don’t push them on it, move on to something lighter instead.
9. If you were stranded on an island and could take three things with you, what would they be?
This is a silly but fun one and will highlight your playful side. We’ve all got things we can’t live without and they say a lot about us. Will it be favorite books, hair care products, a toy with lots of sentimental value?
Almost everyone says their phone, so it’s interesting when someone doesn’t… tough to find people who aren’t glued to their screens these days and it says a lot.
10. What’s the scariest thing you’ve ever done?
This question can go different ways. You could get stories about overcoming fears and making personal progress, like giving a speech in front of 100 people when you have a crippling fear of public speaking.
Or you can get funny stories of stupidity, like climbing to the top of ten levels of scaffolding when you were really drunk and seeing your whole life flash before your eyes.
Either way, good to know, and it will give you a fair bit of insight into your date’s life. Hopefully ‘going on a date with a real creep’ won’t be on their list… it’s pretty easy to avoid these days, given modern safety features!
11. Was there ever an event in your life that defied explanation?
Do you have a spooky experience from the past? An eerie coincidence that could only be your grandma communicating with you from the heavens above? A sighting of otherworldly creatures hanging out in your local forest? Hey, there’s some weird shit out there.
These memories are often quite personal and so someone might feel vulnerable to share,
but a bit of vulnerability is always welcome on a first date. That’s how you get closer after all.
If you can tell they’re taking your question with a pinch of salt, lean in and make some jokes. But if your date takes the question seriously, be sensitive or they might get insulted.
12. Where is ‘home’ to you?
This question can be pretty personal. You might have met your date in the city you both live in now, but you might not know their whole history. Maybe they were born somewhere else or have a heritage that means a lot to them. It might be the place they’ve made the best memories and really want to return to one day.
‘Home’ often means different things to different people, so this question can be great for opening up the conversation and learning more about each other, and getting a sense of what is important in your lives.
13. What’s the worst thing you’ve ever done?
This is a dangerous one! Obviously, you’re playing with a fire a bit here, but it also can be one of the funniest first date conversation starters since some people have some hilarious horror stories.
A surprising number of people will talk about something they did as a child that had a huge impact on them but really isn’t that bad.
Of course, some people will have darker answers, but will they reveal them? It’s fun to confide in each other and will bring you closer, assuming they don’t admit to something really awful. In fact, I should note: still not the time to admit to terrible crimes!
14. What’s something you’re obsessed with?
Some people get obsessed with things. Like, really obsessed. I once dated a girl who collected beanie babies and gave me a tour of her creepy beanie baby-filled apartment, telling me the story of each one in vivid detail. There were hundreds! I had to sit on the floor!
Other people have less intrusive obsessions, like TV shows, or baking bread. Whichever option it is, asking this question is a good way to know if your date is a quirky obsessive (not that that’s always a bad thing) or has any funny stories on the matter. I bring out my beanie baby story so often I might have embellished it by now.
15. How do you love to spend your weekends?
This will tell you quite a lot about a person. Does your date leave work on a Friday and party until Monday? Do they need a lot of quality alone time to recoup from their week, reading at home or catching up on tv? Maybe they have strong family ties and visit often.
Asking this question is a good way to know if your lives will be compatible. If you love to go out with your friends every weekend but your date hates that scene and would rather have cozy nights in, you might not be a good match.
Of course, you’re different people and don’t need to have identical interests, but this is a common point of tension in relationships so why not get in there early and learn if you will gel.16.
16. Where is the worst place you have been stuck for a long time?
Ok, this one is weird because it can be very silly or actually quite stressful. I once got locked inside a bar I worked at and had to sleep on the floor because I couldn’t get out and wasn’t brave enough to break a window.
Once I asked this question on a date and she said ‘Belgium’. Apparently, she was studying there and hated it, but it made me chuckle. The point is, asking this question is a good way to hear some funny stories or at least some interesting stories about a person’s life.
17. What were you like as a child?
Everyone has funny stories from when they were a kid. Maybe you were super annoying and followed your siblings everywhere they went. Maybe you had a lizard who was your best friend. Maybe you were a total nerd and teacher’s pet.
It’s always super interesting to hear about someone’s formative years. Ask this on your first date to get an insight into your date’s past and what they used to be like. Compare it to how they are now!
18. What movie have you seen the most times in your life?
This is different from asking what someone’s favorite movie is, it’s much more revealing.
When asked ‘what’s your favorite movie?’ it’s easy to say something to sound more impressive, something that you kind of wish was your favorite movie but actually went over your head.
If you ask what movie they’ve seen the most, there’s only one true answer. Whether it’s a comforting Disney favorite or a challenging masterpiece they keep going back to, this question opens up discussion about what movies mean to you both.
19. What do you think your most attractive quality is?
If you ask this question and they talk for ages, reeling off a million great qualities about themselves, this might be a sign your date has a bit of ego or might be arrogant.
If, on the other hand, they struggle to say one good thing about themselves this could mean they have confidence issues and are insecure in general.
These might be deal breakers for you, or they might not be, but either way, it’s good to get a sense of how your date feels about themselves as a person.
20. Which person in your life do you talk to the most?
Apparently, we are the product of the five people we spend the most time with. So knowing this about your date will tell you a lot about them, and since they’re close to these people they will feel comfortable talking about them.
Maybe they have a close-knit gang of friends who have been together since school. Maybe they’ve made super close friends while traveling and visit them often, or maybe they get on really well with their siblings and hang out all the time.
Asking this question will help you build a picture of your date’s life and what they’re like, since talking about their nearest and dearest will probably reveal how they think about themselves.
There you have it, 20 great conversation starters for your first date. Read over this list beforehand so a few of them stay fresh in your mind in case the dreaded awkward silence hits. You’re bound to get some laughs, some sincere moments, and you will definitely grow a bit closer to your date. Pay attention to their answers, they’ll come in useful later down the line.