A first date is an exciting yet nerve-wracking experience. It is unlike having small talk at parties and conversations over the phone or chatting on dating apps and social media.
The first date makes you more exposed—your appearance behind the camera, your real reaction sans emoticons to everything, and your physical presence. Will there be a spark? Will you hit it off right away? Most importantly, how do you get the conversation to flow for the entire date?
Arm yourself with a strew of witty, captivating, and fun questions to keep your date entertained and hopefully not making up an excuse to get away from you.
Funny first date questions
It’s quite likely that you were never the class clown and you’re not known as the funniest person on the planet, but we all love a good laugh. When you get your date to laugh, you shake off the nerves so you’re more comfortable on your first date. It all depends on the perfect timing so you don’t risk blurting out a joke that’s out of place or downright disrespectful. Let’s kickstart the date with these totally relatable hilarious questions to ask on a first date:
Do you consider a hotdog a sandwich?
Have you ever wondered how many chickens there are in this world?
Have you ever tried to sell your organs a week after payday?
Did you ever think Facebook messed up with making people “Seen?”
Have you ever pushed a pull door and someone behind you had to say you need to pull it?
Have you ever had a difficult time opening easy-open packages?
Do you like music that brings back the good old times like when we were still not alive?
Have you ever caught yourself sounding like your mom/dad when you’re mad?
Can you belly dance as if your life depended upon it?
What would you say to the president if you ran into each other?
Do you think people-watching is a universal game to pass the time?
What is the funniest name you’ve ever heard?
What is the best WIFI name you’ve ever seen?
What’s the silliest trend you ever followed and later regretted?
What song do you wish would play every time you do something kick-ass?
How do you respond when you’re in a public restroom and someone knocks on the door?
Do you ever squat when you take a “groufie?”
Have you ever taken a selfie after checking yourself out in the mirror and can’t get the shot you see in the mirror?
Have you ever went back to sleep to find out the ending of your dream?
Now the first date is all about getting to know your date, what it’s like to be with their company, and such. So, here are funny getting to know you first date questions to ask:
Do you have a dedicated chair for clothes that are too dirty for the closet but too clean for the laundry?
What was your face like when you got caught staring at your crush?
What’s your signature dance move?
If you won a trip to anywhere in this world, where would you take me?
Could you go for a week without your gadgets or apps or your gaming consoles?
If you got arrested, what would your family and friends assume you’ve done?
If you got mistakenly placed in an asylum, how would you prove you are really sane?
If you got blasted into the past, how would you prove you are from the future?
What are the things you could buy that would make a cashier laugh out loud?
Do you have a nickname for your boss/teacher that only you and your coworkers/classmates know?
Do you fold your pizza before you eat it?
What is the funniest thing you’ve seen a stranger do?
Fun first date questions
To get the conversation flowing, you want to have a list of questions on hand that will make you out to be an adventurous and fun-loving person. Discover if your date is fun to be with, a daredevil, or a bore. Here are some fun get to know you questions you will want to ask your date:
How far into a movie before you finish a bucket of popcorn?
What is the one food you would never dare eat?
On a scale of 1 to 10, how strict are your parents?
If you can change your name, what would you change it to?
What is the story behind your nickname?
What is the most adventurous thing you’ve done yet?
What did you decorate your bedroom with when you were a teenager?
What was your favorite toy when you were a kid?
Which toy were you always scared of?
Which cartoon character do you wish you could be?
Do you have a favorite pick-up line?
What is your current favorite dance playlist?
Let’s go into theoretical scenes that may or may not happen in this lifetime. How game is your date when it comes to imagining fun scenarios like these?
Would you like to time travel like Hiro Nakamura or teleport like the “Jumper” David Rice?
Which is the worst sequel you’ve ever seen?
Which movie do you wish had a sequel?
Which movie do you think should be a TV series?
Which movie do you think is better than the book?
If someone asked to be your apprentice, what would you teach them?
If you could be the first in the world to do something, what would it be?
When was the last time that you did something for the first time?
If your life were turned into a movie, what would its title be?
Which actor would best portray your life story in that movie?
If you got stuck on a deserted island, what are three things you are sure you brought with you?
What would you do if you had no electricity for the whole day?
What is the first thing you would do if you became the president for a day?
If tomorrow you won big in the lottery, what is the first thing you would spend on?
If you could make up a holiday, when would it be and what would it be like?
If everyone held a day in your honor, what would you like everyone to do?
Can you make a fun impersonation of any TV/movie character?
To make your fun questions more romantic, you may want to involve yourself in the scenarios. Can your date picture you out in the fun scenes? This is also a good time to gauge whether or not you will be having a second date anytime soon. Go ahead and have fun asking these questions:
If you could spend the day talking to only one person, who would it be?
What is on your bucket list and which of those do you think we can do together?
What do you like and don’t like about dating?
What is something you always wanted to try and what’s stopping you?
What is a fun way to spend a weekend?
If we starred in a movie together, what would the story be?
What is the wackiest name you could think of to give your child?
Questions to ask a guy on a first date
Girls, don’t worry. For sure the guy is more nervous than you are when it comes to the first date. If you really want to get to know the guy, you’d want to get the conversation flowing especially when he starts fumbling for words. Let’s start with easy questions about their favorites:
What is your favorite type of music?
Which holiday do you like the most?
What is your favorite show on Netflix?
What is your all-time favorite movie? What is your favorite line from that movie?
What film genre do you favor the most?
Who is your favorite singer/band? Which of their songs do you like best?
Where is your favorite place to hang out?
What is your favorite fast food chain? Do you have a go-to meal every time you eat there?
If you could only eat one food for the remainder of your life, what food would it be?
Who is your role model?
Where is your favorite bar/pub? What is your go-to cocktail there?
Who is your all-time favorite athlete?
What is your favorite ice cream flavor?
What is your favorite year yet?
Now guys will forever be boys or at least it is said that most guys don’t mature until age 43. You can still certainly ask about games and talk about childhood and such with a guy on your first date. Some good questions to ask are:
Are you a cat guy or a dog guy?
Would you rather play Monopoly or Jenga?
What is your fondest memory of a pet?
When you were a little boy, what did you want to grow up to be?
If life was a video game, what would the cheat codes be?
What’s a rule you hated as a kid that you swear you’d make your kids follow?
What kid’s show do you still watch?
Who was your childhood best friend? Are you still friends now?
Have you ever played a prank on your teacher?
What is something sneaky you got away with?
Did you ever sneak out of school without getting caught?
Have you ever lied to cover up for your friends?
What is your fondest memory of your dad?
Who do you consider your real-life hero?
Which of your siblings or cousins are you closest to?
You can also ask them more getting to know you type of questions to make them feel at ease talking with you. Here are some fun questions to ask your date:
Do you think superheroes should have capes or no capes?
If your life was turned into a movie, would you like it be a Hollywood movie or a cartoon?
What do you do when you can’t sleep?
What song did you play on repeat the most?
What movie did you watch in theaters more than once?
What reality show would you like to be on?
What was your first-ever first date like?
If you could have one wish, what would you wish for?
What do you usually do on a Saturday morning?
Is there a movie character you want to play?
Interesting first date questions
Did you know that smart is the new sexy? If you can come up with questions that are well thought out, you will certainly exude a level of attractiveness to your date. Here are some sample questions:
What would you do with an hour of free time?
Are you doing what you are passionate about?
What was your environment like growing up?
What is your plan like for the next three years?
Have you ever traveled long-distance by yourself?
If you can have any job you’d like in the world, what would it be?
When do you feel the most relaxed?
What would you like for people to focus more on about you?
What is one thing about you that would surprise me if I found out?
Can you do something not everyone can do?
What is the best present you’ve received? How about the best gift you’ve given?
What was your best Halloween costume?
What is your fantasy travel experience like?
What is the best advice you’ve ever given? How about the best advice given to you?
Would you consider yourself lucky?
What happened on your best birthday yet?
What is the most courageous thing you’ve ever done?
Have you ever saved anyone from an accident (could be an animal too)?
Would you rather go on a cruise or backpack to a foreign country?
Can you cook your favorite meal?
Have you ever cooked a special meal for your family?
Have you ever planned a birthday surprise?
What is one piece of advice you’d give to your younger self?
What is one thing I could never have guessed about you?
Who is your go-to person?
If you could recreate the food pyramid, how would your version look like?
What is the story behind one of your tattoos?
Do you still have a scar from your childhood?
Consider asking about their philosophy in life too. You’d be astounded to know how your date thinks about certain matters that may either be trivial or important to you. Keep in mind that the questions should be open-ended to keep the conversation flowing and none of those answerable by a nod or a shake of the head. Here are some good ones:
What is your philosophy on giving tips?
What food is highest on your food hierarchy?
Do you think men and women are equal?
What is your philosophy on discipline?
Are you saving for a big-ticket purchase?
What are your go-to words of encouragement?
What do you say to yourself when you’re feeling afraid?
What do you do when you lose hope?
What is one thing people do every day that you wish we’d all stop doing?
Have you ever given up on something you wanted to have?
What makes you quit?
How do you teach a person something you know?
Would you rather be a leader or a follower?
What is one rule you wish everyone would live by?
How far would you like to travel?
What’s the best way to travel?
What do you look forward to every day?
Why do you do what you do now?
If you weren’t in this profession, what would your life be like?
First date questions to ask men
If you are dating to get into a serious relationship, then you should have no qualms about asking questions that will get into the heart of your date. Find out if from the onset if you are on the same boat as your date. Here are three important questions to ask a man on a first date:
When were you last in a relationship?
What are you looking for in a partner?
What do you see yourself doing in the next 5 years?
Those three questions will hopefully save you from wasting the next hour or so on a con-artist or a guy who is already married. If, however, you wish to spend some time having fun and a casual conversation with your date (no holds barred), go ahead and get to know the man you’re dating with these questions:
Do you prefer wine or beer?
Which board game are you good at?
Can you name three good qualities about you aside from your looks?
Do you like playing music in the car?
Do you like going on long road trips?
What is the last movie you’ve seen alone?
What is the last song you danced to?
What skill are you so good at?
What is a good long-distance trip to go on over a weekend?
What do your weekends look like?
Alright, now it’s time to get to know the family and try to see if your date is husband-material. You will want to check their family background, childhood, and future plans for building a family. Here are questions to help you get those answers you need:
What do you like about the place you grew up in?
What was the last thing you bragged about to your parents?
What are you most proud about your family?
Who are you closest to in the family?
Do you live near or visit your family often?
What is your favorite family tradition and do you still do it every year?
How long did your longest relationship last?
Do you have or want to have kids?
What job were you happiest doing?
What is the best thing about your current job?
What happens in a typical week for you?
Do you consider yourself as a spender or a saver?
What are your top priorities on your bucket list?
You may also want to get a feel of what it’s like living with that person. Here are some good first date questions to ask if you want to settle down anytime in the near future:
Do you make your bed every morning?
What do your morning and evening routines look like?
Is there any new habit you are trying to build into your daily routines?
What is one chore you enjoy doing?
How do you feel about wearing sweatpants?
Do you often go out on weekends or binge watch on Netflix?
How often do you spend time outdoors?
How much time do you spend on your passions?
What is your pet peeve when it comes to your partner?
Do you like planning vacations or enjoy the spur of the moment?
Who would you say influences you the most?
Who do you look up to?
Questions to ask a woman on a first date
You can pretty much ask her anything on your first date except for perverted and creepy questions. If you really like this girl and would like to ask her out on a second date, you may want to know about her favorites. That way, you can better plan your next date that is tailor-fit to her personality. Here are some questions to ask to know what a woman wants:
What is your go-to homemade dish to cook? Is that your favorite food too?
How proud are you of your culinary skills?
What is one dish you would love to try?
Do you have a favorite restaurant for ordering take-out?
Do you dine out often?
What is one type of food you will never eat even if it’s the last food on Earth?
Do you like spending time with animals?
What movie genres do you enjoy watching?
Which fictional character do you find highly attractive?
What TV series can’t you live without?
What is your sport?
Do you have a favorite sports team?
Do you like being given flowers?
Do you prefer coffee, tea, wine, or juices?
You can also test the fun factor of your date. How fun is she to be with? Also, you may want to know her family background. Such questions as these would lead to what you desire:
If you got stranded on a deserted island, how will you survive?
Who do you want to be stranded with?
What are you most afraid of?
What were you like as a young girl?
Which among your family members is the most protective of you?
How would your closest friends describe you?
What do you do with your friends for fun?
You can also gauge the girl’s expectations of an ideal partner and of a relationship. This is also the time to gauge whether or not you are ready for this type of commitment. If not, it’s best not to break the girl’s heart and not to leave any signs that can be misconstrued. Anyway, here are questions you can ask about relationships:
What would you consider as a perfect date? How about the worst date?
What does your best friend look for in an ideal partner for you?
What does your family look for in an ideal partner for you?
How about you, what do you look for in a man?
How do you feel about having kids?
What do you think is a man’s role in the household? How about the woman’s?
What can’t you stand living with?
How can I be of great help to you in your life right now?
What are your long-term goals in the next 3 to 5 years?
What do you consider are top priorities in a relationship?
What are your priorities right now?
It is said that men and women have different goals when it comes to the first date. You may either be looking for friends, someone to pass the time with, or long to be in a relationship anytime soon. If you are in the mood for flirty questions to ask a girl on a first date, here are some questions to try:
What made me attractive to you?
What is your biggest turn on?
Should guys always be the one to make the first move?
What was your first love like?
What was the most romantic gesture a guy did that really impressed you?
What was the craziest thing you ever did for a guy? Would you do it again?
If you could teleport to any place in the world right now, which place would you choose?
If you could spend an entire day with me, what would you like for us to do?
Weird first date questions
We once saw a viral post that goes: “normal is a setting on the washing machine.” So embrace your weirdness because that is what makes you so unique. When no one is watching, we let our hair loose and just be ourselves. If you want to gauge a person to see whether they are fake or genuine, here are some questions to ask about their weirdness:
What is a word or a phrase that you say a lot?
What are your quirks?
What one type of food will you force everyone in the country to eat (including me and you)?
What is your favorite song to sing in the shower?
Do you have a victory dance?
When did you last scream at the top of your lungs?
Did you ever shout out loud that you like someone?
Did you ever secretly have a crush on one of your best friend’s date/partner?
What is the best and worst way to go from point A to point B?
What place do you picture yourself at whenever it’s hot and humid?
What is the weirdest place that you look into when you lose something?
Do you ever hypothetically blame someone in your head when you lose something?
Now let’s not be too serious and turn this into a fun date. Here are some fun questions that may sound weird to your date:
Who do you secretly want to punch in the face or kick in the shins?
If you have the power to bring back one famous person to life, who would you bring back?
How would you survive a zombie outbreak?
Which Hogwarts house would you want the sorting hat to send you to?
If you would be forced to have a date with anyone here today (a public place), who would be the worst choice?
What food would taste weird if it was in a different color?
If you could pimp my ride, what would you add to it?
If you could be a spy, who would you want to spy on?
Which are friendlier—pets or humans?
Which one show/movie can’t you stand watching alone?
If you have the power to shapeshift, what big thing would you turn into?
If you could live like Indiana Jones or Lara Croft, would you?
Now let’s go on to weird questions that you should probably ponder about in life if you get the time. Here are some questions we’ve poured over on rainy days and random moments:
If you could turn into something that remains in the planet after you die, what would you turn into?
Are you happy with who you’ve become?
Do you think we need to be insane to be creative?
What was your worst creation when you felt uninspired?
Can you tell me your life story in seven words?
What do you dislike so much but don’t know why?
Which animal if overpopulated would bring about the extinction of man?
If you can construct a bridge with food, what would it be made of?
If you could live in a house made of food, what would you use to build your house?
If you could move one landmark on Earth to a different place, what would it be and where would you move it to?
What would people say is the weirdest thing about you?
Keep in mind that this list is just a guide to prepare you for your first date and the next dates up ahead. If you really want to score a second date, you can’t bring out a list of questions and just dictate them to your date. You wouldn’t want to sound like an interviewer on your first date. Instead, think of the questions here as your cheat sheet to turn those anxiety-filled first minutes and awkward pauses into fun moments.
The first date should last at least a good two to three hours. Don’t worry as the moments will pass by quickly when you’re having a good time and a nice exchange of conversation on your first date. If your date’s answers are short and seemingly disinterested or you find you don’t have much in common at all, don’t worry. We all have our share of disconnected and boring dates.
You can save that experience to tell your next date of your worst first date experience ever. Remember not to trash talk anyone, not to ask for pity, or to be pushy and insensitive when having a conversation with your date. Be mindful of your date’s response to questions that you can take a cue from for your next date. Good luck and have fun!