150 Uncommon First Date Questions – Easy Conversation

Entertainment By James 

150 Uncommon First Date Questions – Easy Conversation

Entertainment By James 
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Let’s be honest, first dates are always among the most awkward moments in a person’s life. It doesn’t matter if you’re 14 or 44, you’re always a little unsure of how to approach things. Most of the time, you’re going to be a little nervous as well, which doesn’t help matters. The funny thing is that there are countless conversation topics that are appropriate for a first date, as well as a near-endless list of questions you can ask. The trick is to have a few in mind ahead of time so you can remember them and have something to say when you get on the date. If you’re having any trouble, here are some great, uncommon questions and conversation starters for first dates.

Table Of Contents


  • Getting Started
  • Digging A Little Deeper
  • Critical Thinking
  • I Want To Know You
  • Food And Stuff
  • Time To Laugh
  • Pop Culture
  • Way Out Of Left Field


Getting Started


1. What do you do in your free time?

Okay, so this is a little cliche, but you have to start somewhere, right?


2. How many siblings do you have?

This is another traditional first date question, but it’s an easy way to start a conversation, assuming you can ask some follow-up questions based on the answer.


3. What was the last book you read (and liked)?

It’s a certifiable fact that people who read are more interesting, which is why it’s good to ask what your date likes to read.


4. Who’s the most interesting person you’ve ever met?

You never know where a person has been or who they’ve met until you ask.


5. Where’d you go on your last vacation?

What are the odds of a person going on a boring vacation? Find out the last cool place your date went and you two will be swapping interesting stories in no time.


6. What’s your biggest guilty pleasure?

This might be a little forward for a first date, but you can learn a lot about someone from their answer.


7. Do you have any pets?

If there’s any chance for you two to become a couple, you should be on the same page when it comes to pets.


8. Do you prefer to spend your time indoors or outdoors?

This seems like a simple and boring question, but you can tell a lot about a person by whether they’re outdoorsy or like to stay inside.


9. What’s the worst thing to ever happen to you on a date?

If you need a little confidence boost on a first date, it’s good to know just how low the bar has been set by some other loser.


10. Do you prefer the mountains or the beach?

Most people will probably say the beach, but it never hurts to ask just so you can get on the same page.


11. Can you keep a secret?

To be clear, you’re not sharing a secret on a first date. But you should try to find out if this person is capable of keeping your secrets if it should come to that.


12. What’s your all-time favorite board game?

At first glance, this may seem like an odd question, but if you think about it, someone’s favorite game can be a little revealing.


Digging A Little Deeper


1. What’s something you always wanted to try but haven’t had the chance?

This is a good way to fish for something to do on your second, third, or fourth date.


2. What’s one kind of weird thing that really interests you?

This isn’t the same as sharing a secret, but asking this is a good way to show your date that you’re not judgmental.


3. What was the strangest night of your life?

This just seems like a good way to start swapping funny and interesting stories, which is not a bad way to spend a first date.


4. Who’s your favorite author?

If your date doesn’t have a favorite author, there’s something terribly wrong. Otherwise, this says a lot about a person.


5. What’s your favorite Olympic event?

First, you have to find out whether they prefer summer or winter. Then you can find out what event they look forward to the most and why.


6. What country would you most want to visit?

We all have travel aspirations, and this question will tell you just how ambitious of a traveler your date is?


7. Do you have a favorite quote or saying?

Not everyone walks around with a favorite quote in their head, but if your date is interesting to talk to, he or she should be able to come up with one.


8. Where did you see your most memorable sunset?

Answering this might take some thinking, but there’s probably a good story here.


9. What’s your favorite outdoor activity?

This might be a little cliche, but you have to find out if your date likes to just lounge around in the sun or actually be active.


10. What’s the most spontaneous thing you’ve ever done?

Surely, there’s an interesting story here; otherwise, your date might be the most boring person in the world.


11. What’s the funniest thing you’ve ever seen?

Again, you’re just trying to get your date to share an interesting story with you so you can get the conversation flowing.


12. Would you consider yourself a night owl or an early bird?

This question is important to ask just so you know how compatible you two are together.


13. What’s the worst online dating experience you’ve ever had?

Everyone has done online dating at least once, and this is another good way to set a low bar for yourself.


14. Other than home and work, where do you spend most of your time?

This seems like a standard and boring first date question, but it tells you a lot about where your date likes to hang out.


15. What household chore do you hate doing?

You don’t want to make a habit of bonding with your date over things that you hate, but this is one of the exceptions.


16. What do you do to unwind and relieve stress?

This doesn’t seem too revealing, but it’s another good way to get to know someone.


17. How much do you value your personal space?

To be fair, this is an odd question, but it will tell you how much your date is down with PDA.


18. Are you close with your family?

Yes, this is another cliche question, but it’s something that you’ll have to ask at some point.


19. What made you say yes to this date?

In case you’re a little insecure about yourself, this is a good way to get a confidence boost. Surely, there’s some reason why your date agreed to see you.


20. How eager are you to get married?

You probably don’t want this to be the first question you ask, but it can be good to learn a person’s bottom line right away.


21. If you were giving me a tour of your hometown, what would be the first stop?

If you and your date didn’t grow up in the same place, this is a great way to help learn about their past.


22. What was the best part of your day?

Okay, so this is a silly question, but it’s one you can use if you get a little desperate for conversation.


23. Would you rather go on an awesome road trip or relax at a five-star resort?

To be fair, it’s hard to pass up on a five-star resort. But someone who’s adventurous and exciting to be around will surely pick the road trip, so you can learn a lot about your date from this question. (See here for more hard would you rather questions)


24. What was your craziest experience with illegal substances?

We’ve all had some experience with drugs at some point, right? Good or bad, there’s probably an interesting story to be told.


25. What super power do you wish you had?

This is another silly question, but it’s also a revealing one.


26. Are you spontaneous or do you need a routine?

This question will help you learn whether or not you and your date will be compatible long-term or if you have to rely on the old adage that opposites attract.


27. Who do you call after a bad day?

This is how you’ll learn the person your date is closest to and perhaps open up the conversation about friends and family.


28. What’s your biggest pet peeve?

It’s best to find this out as soon as possible so you can avoid doing it on a first date. This is definitely one of the best uncommon first date questions as you’ll be able to figure out how not to annoy them.


29. What was your most memorable birthday party?

Everybody must have at least one memorable birthday party. If not, there’s something wrong with your date.


30. Do you believe in ghosts?

If your date is down to spend the night talking about ghosts, she’s a keeper. But not believing in ghosts isn’t necessarily a deal breaker.


31. What’s the worst crime you’ve ever committed?

Sure, this question implies that your date has committed a crime at some point. But nobody’s perfect, and there’s probably a good story.


Critical Thinking


1. If you could give yourself a nickname, what would it be?

How many people have a chance to give themselves their own nickname? Your date will be grateful.


2. If you had to start a business, what kind of business would it be?

This is a good way to get some insight into what your date really wants to do rather than asking about her current job.


3. If you had 24 hours to spend $10,000, what would you do with it?

This isn’t the most clever question, but it should get your date talking and lead to an interesting conversation.


4. What’s your dream job?

You should always be asking potential partners about their hopes, dreams, and aspirations. That’s Dating 101.


5. Describe your perfect vacation?

Does your date have a vision of the perfect vacation or at least a good imagination? Here’s a good way to find out.


6. What’s your idea of a perfect Sunday morning?

This is another good way to find out what your date is really like and what they really want to do.


7. What’s the worst advice someone has ever given you?

This topic may not lead anywhere, but it should be good for a laugh.


8. If you didn’t have to sleep, what would you do with all of the extra time?

Sure, this question is a little weird, but it should help to keep your date engaged.


9. If you were forced to spend your life savings on one thing, what would it be?

Sure, financial questions are weird for a first date, but this one should be a good exception.


10. If you could turn into an animal, what animal would you be?

We’re definitely a little off base with this question, but most people live animals, so your date should enjoy this odd request.


11. What would be your dream city to live in?

Again, dating is all about finding out your partner’s hopes and dreams. Plus, what if you and your date have the same dream city?


12. Would you prefer to be rich or famous?

This isn’t an easy question by any stretch, which is why it should be an interesting proposition for your date.


13. If you had one year to live, how would you spend it?

To be fair, this question is a little morbid, but if you’ve gotten off to a good start, this can be an interesting question to throw at your date.


14. If you could go back in time to observe one historic event, what would it be?

This is another weird one, but unless your date has a head full of rocks, she should have an interesting answer that will get the conversation going.


15. What’s one skill you wish you had?

We’re back to wishes, so this question definitely has a good chance to get a conversation going.


16. What’s one thing you don’t like about me?

This is definitely taking the unconventional route, but it can be a good way to see where you stand and gauge how the date is going.


17. Who was your favorite teacher in school?

There’s nothing wrong with a little trip down memory lane to help you get to know someone better.


18. Do you think things out or act based on emotion?

This question definitely starts to go a little deeper. Eventually, you should learn this on your own, but it doesn’t hurt to ask.


19. Are you trusting of strangers?

Does your date believe that strangers are just friends you haven’t met or is she a little more cynical? Just try not to sound too creepy when you ask.


I Want to Know You


1. What’s one talent you have that nobody knows about?

You’re asking your date to divulge a secret to you, so you have to go about this carefully.


2. What was your favorite place to go as a kid?

This is a personal question, but it should make your date happy to take a trip down memory lane and pleased that you’re interested.


3. What’s one thing you’ve done that you’ll never do again?

Hopefully, the answer is something like skydiving or bungee jumping. Either way, it could be the start of an interesting conversation.


4. What’s the most memorable thing to happen to you over the past month?

This may seem like an odd question at first, but your date should be taken aback by you asking.


5. What’s one wrong assumption people tend to make about you?

Your date may need to think about this for a minute, but that’s not a bad thing and it’s a good way to get to know her.


6. Who’s Your best friend and why?

If you want things to go beyond a first date, you’re eventually going to get to know your date’s friends, so you might as well start early.


7. What do you value most in a friend?

If you know what your date wants in a friend, you may have a window into what she likes in a romantic partner, so this can be an important question.


8. Who has influenced your life the most?

The answer to this could be just about anything, and that makes it a good way to get to know your date better.


9. Who is your role model for both work and life?

Some people have work role models and life role models, so why not ask about both?


10. What’s your favorite holiday memory or tradition?

This is another question that will take your date on a pleasant trip down memory lane, which should put her in a good mood.


11. What’s your spirit animal?

Come on, how could this question not lead to a fun conversation?


12. What’s on your bucket list?

Learning the items on someone’s bucket list is a great way to get to know them, so this is kind of the perfect uncommon first date question.


13. What’s your favorite place that you’ve lived?

If your date has moved around a lot, it’ll be interesting to ask her about the places she’s lived previously and what she liked about all of them.


14. What would you say is your biggest accomplishment?

Nothing will make your date feel better than the chance to gloat just a little bit.


15. What did you want to be when you were growing up?

Maybe this is more of a second date question, but it won’t hurt to ask about your date’s childhood the first time you get together.


16. What movie changed your outlook on life?

Everybody has that one movie that always stands out to them, and finding that out will tell you a lot about your date.


17. What time of day do you look forward to the most?

This seems like a simple question, but it’s not something that most people are going to ask on a first date, which is why you should become the exception.


18. What’s the nicest thing you’ve ever done for somebody?

You can also ask the nicest thing anybody has ever done for you, but why not see how much good your date has done for other people.


19. What is your most haunting memory?

This isn’t a question to ask lightly, but if you don’t mind getting a little deep, you can take a chance and ask.


20. When was the last time you cried?

Again, this is an odd question for a first date(that’s why this is a list of the best uncommon first date questions), but under the right circumstances, it can work.


21. Where is the most romantic place you’ve ever been?

If she says “right now,” you know things are going well. If not, you’ll know the level of romance you have to reach on your subsequent dates.


22. When was the last time you got lost in your thoughts?

This definitely isn’t an ordinary first date question, but it’ll prove to your date that you genuinely want to get to know her.


23. What’s your most unpopular opinion?

This should be a fun question, but also one that tells you a lot about your date.


24. What day of your life would you want to re-live over and over again?

This is another question that has to be asked under the right circumstances because it’s kind of a bummer. But if the date is going well, it’s a great way to make a strong connection with your date.


Food and Stuff


1. What’s your favorite kind of international cuisine?

Does your date prefer Chinese, Mexican, Italian? You have to find out early if you two are going to be compatible when it comes to eating out.


2. What meal is your favorite to cook for yourself?

In this case, any answer is the right answer.


3. What’s your favorite restaurant?

Make sure you’re paying attention to the answer so you know where you go on your second date.


4. Do you order the same thing at your favorite restaurant or do you like to try new things?

This question seems innocuous, but you should know if your date likes trying new things or is boring and likes the same old thing.


5. What’s your biggest comfort food?

If you want to go out on multiple dates, this is information you need to have.


6. What’s your favorite ice cream flavor?

Do you know the perfect nightcap on a first date? Going out for ice cream. This is more information you’ll need to have.


7. What ice cream flavor doesn’t exist that you think should?

If you’re lucky, your date is creative enough to come up with something good. If you’re really lucky, she’ll have an idea that will make both of you millionaires.


8. What’s one weird food you’ve eaten that you actually liked?

Brace yourself for the answer and don’t be too judgmental. Remember, you asked.


9. What are your favorite pizza toppings?

If you two aren’t compatible when it comes to your pizza toppings, why even bother continuing with the date?


10. Do you prefer cooking for yourself or going out to eat?

There’s no wrong answer to this question, but it’s definitely good to know one way or another right away.


11. What fancy and way-too-expensive coffee drink is your favorite?

Lattes, cappuccinos, espressos, and macchiatos; there are so many choices, so you need to know what she likes so you know what to order for your date the next morning.


12. What’s the most memorable meal you’ve ever had?

This sounds like a round of 20 questions, but since it’s a pleasant memory, your date should welcome the question.


13. Beer, wine, or shots?

Simple enough.


14. What’s your favorite alcoholic beverage?

Once you’ve determined whether your date prefers beer, wine, or shots, it’s time to get a little more specific.


15. Do you prefer chocolate or caramel?

Just kidding, the answer is obviously chocolate.


16. What’s your favorite smell?

This isn’t the best icebreaker, but once you and your date get a little more comfortable with one another, it could be a fun topic to try.


17. What’s your favorite type of cheese?

We all like cheese (sorry, lactose intolerant people), but is your date more into cheddar or pepper jack? It’s an important question.


18. What’s one dessert you could eat every night if you could?

Sure, this is basic first date material, but it never hurts to know.


19. Would you ever consider being a vegetarian or vegan?

For the record, there’s nothing wrong with either one of these, but if there’s going to be a second date, this is good information to know.


20. Do you prefer to eat healthy foods or just work out like crazy?

Hopefully, your date is down with at least one of these two options. If not, you may be dating a total slob.


21. What foods do you refuse to eat?

Dietary restrictions (even self-imposed restrictions) don’t make for the most scintillating conversation, but it’s still good information to have.


22. Coffee or tea?

Of course, the most investing answer to this would be “none of the above.”


23. What’s the most embarrassing thing in your fridge right now?

Admittedly, this is kind of a weird question, but it has the chance to spark a fun discussion.


Time to Laugh


1. What’s something ridiculous that you’re afraid to admit?

This may seem like a penetrating question, but really you’re just trying to get a cheap laugh.


2. What’s the one fad that you never fully understood?

Image how hilarious it’ll be when your date explains to you that she never understood the beanie babies craze or why boy bands were so popular.


3. What movie did you think was so bad that it bad you laugh unintentionally?

Okay, so your date probably hates this movie, but if it makes you both laugh, it’ll be good first date material.


4. What’s the dumbest pickup line anyone has ever said to you?

This could bring up a bad memory, but if it’s done in the name of humor, your date shouldn’t mind too much.


5. What’s the craziest law you would want if you ruled the world?

You shouldn’t do too many hypothetical questions on a first date, but this is a fun one, so it can be an exception.


6. What’s been the most embarrassing moment of your life?

This may seem like a dumb question, but as long as enough time has passed, tragedy will turn into comedy.


7. What’s one weird fact you’ve learned from a Snapple cap?

Everyone has learned something crazy and stupid from a Snapple cap. If you and your date can’t remember something specific, just try making something up; it should get a cheap laugh.


8. What’s the strangest set of circumstances that led to you becoming friends with someone?

Admittedly, this question is oddly specific but should lead to a funny story.


9. What’s the most embarrassing nickname you’ve ever had?

You don’t want to press for too many embarrassing details on a first date, but this should be fine if you two can laugh about it.


10. Do you prefer knock-knock jokes or “that’s what she said” zingers?

You should always be trying to make your date laugh, so it makes sense that you would try to find out what’s going to make her laugh.


11. How many marshmallows can you fit in your mouth at once?

Yes, this is stupid, but it’s also funny too, right?


Pop Culture


1. What’s your preferred streaming service?

This is something you have to sort out right away. Are you going to Netflix and chill or does your date go home to Hulu or Amazon Prime?


2. Who was your first celebrity crush?

This is usually a fun but slightly embarrassing question that should be standard on a first date.


3. What’s your favorite song to sing in the shower?

This question is perhaps a little too familiar for a first date, but as long as you don’t ask it in a creepy way, it should be fair game.


4. What’s your favorite movie in the Star Wars series?

If your date says Episode I, II, or III, you should probably just part ways now because it’s not going to work out in the long run.


5. What celebrity would you want to be best friends with in real life?

Being best friends is different from having a crush. You want to know who your partner wants to be her partner in crime.


6. What’s your favorite all-time movie?

This may be the most important question you ask all night. Technically, there are no right or wrong answers, but let’s be honest, not all answers are created equal.


7. What’s your favorite TV show to rewatch over and over again?

This question isn’t necessarily about what shows your date likes to binge watch; rather, older shows they like watching in syndication.


8. What’s your favorite song to listen to on repeat?

Just to be clear, this isn’t necessarily your date’s favorite song, just one she enjoys listening to over and over again.


9. Who’s your favorite celebrity?

Okay, this is the question that asks for your absolute favorite celebrity.


10. Describe your musical taste by naming three artists?

This could be a challenging question to answer, but it’s crucial if you and your date want to get to know each other.


11. What podcast do you listen to religiously?

Everybody has a favorite podcast nowadays, and learning that information is almost as important as learning about someone’s favorite movie or TV show.


12. What’s one TV show you would bring back if you could?

We’re talking about classic television with this question. That means your date’s answer better not be a show that was made this century.


13. Who is your favorite Disney villain?

Asking to name your favorite princess is a little cliche, don’t you think? It’s far more interesting to ask about someone’s favorite villain.


14. Who would you want to play you in a movie about your life?

This is a great way to find out how somebody views themselves. Do they pick an A-list star or a more modest selection?


15. Would you rather go on Jeopardy or Wheel of Fortune?

If your date says Jeopardy, it means they think that they’re smart; otherwise, they settle for the Wheel.


16. Which Power Rangers character did you identify with the most?

Not knowing the Power Rangers well enough to answer this question could be a dealbreaker.


17. If you were in The Matrix, would you choose the red or blue pill?

To be honest, I don’t remember which pill is which, but as long as either of you has seen this movie, it can be a fun question.


18. If you were in the Village People, what would be your character?

This question is far more revealing than you may think. Does your date see herself as more of a police officer, cowboy, or construction worker? Important question!


Way Out of Left Field


1. Who’s the strangest person you’ve ever met?

Sometimes strange people are the most interesting, so don’t think of this as an insult to the person you name.


2. What would you prefer, a fast car or fast Internet speed?

If your date says car, it means she’s into flashy things, but if she wants fast Internet, she’s all about getting stuff done.


3. Do you believe in love at first sight?

You don’t always want to ask this question on a first date, but if things are going well, you might want to sneak it in there.


4. If you had to get a tattoo right now, what would it be?

If your date doesn’t already have a tattoo, this question isn’t a big deal, but if it would be her first, her answer will probably be interesting.


5. Ever witness a murder?

If things are getting a little boring and you want to keep your date on her toes, throw in this question. The answer is probably no, but you never know.


6. Would you ever dump me for not liking one of your Facebook posts?

Do you really want to date someone who takes social media so seriously? This is something you need to know right away.


7. If tomorrow was a holiday, what would you do?

This question isn’t all that intrusive, but it does tell you how she likes spending her free time.


8. How would you prepare if you knew the zombie apocalypse was coming?

When the zombie apocalypse comes, you want to be dating someone who’s going to be prepared.


9. If a genie gave you three wishes, what would they be?

Yes, this question is a little silly and childish, but you can really get to know someone based on the answer.


10. Do you believe in aliens?

If you both agree on this subject, that’s great. If not, it’ll make for a fascinating and memorable debate on your first date.


11. How do you think you’re going to die?

This one is a bit morbid, but if you’re desperate for something interesting to talk about, you can keep it in your back pocket.


12. What do you think are the chances this becomes a one-night stand?

Don’t act like both of you didn’t think about this before the date. You might as well be honest and lay your cards on the table.