275 First Date Questions That Aren’t Awkward

Don’t get caught with an awkward silence on a first date! These 275 first date questions will help you break the silence, get to know one another, and have a great time!

We have all been there! The dreaded first date when you are trying desperately to think of something to say or something to ask! If this is you, don’t worry because we are here to help! We have rounded up the best first date questions that are perfect for blind dates, first dates with acquaintances, or even a first date with your best friend!

How to Use these first date questions

It is important to know how to use these first date questions. You don’t want to pull out your phone and start reading down the entire list, question after question. This will make it even more awkward!

First, be prepared. Study this list ahead of time. Find 4-5 questions that you really want to ask. Remember these.

When you are on your date, start with small talk. Once the conversation fizzles or becomes awkward, ask a question from the list. Once you ask it really listen to their answer. See if you have any similarities with the answer that they say to you. If o, once they are done, point it out. Continue using this question to spark more conversation.

When you need another ice breaker, ask one of your other questions. These first date questions will be the key to a fun night even if you opt to never go on a second date with them!

Do you love questions? Don’t forget to stop by and check out our Questions to Ask a Girl or our questions to ask a guy for even more ideas!

First Date Questions

• What is your favorite film in the comedy genre?
• What was the first book you read that really stuck with you?
• What do you like to do in your free time?
• Are you more of an indoors or outdoors person?
• Who is the most fascinating person you’ve met?

• What was the last book you really got into?
• Are you an introvert or an extrovert?
• What are some movies you really enjoyed?
• What amazing adventures have you been on?
• What is one activity that you would like to do on a date?

• Who are the people in your life who have a special place in your heart?
• What pets have you had?
• What are your favorite alcoholic and non-alcoholic drink?
• What are you kind of obsessed with these days?
• Where have you traveled?

• What’s your favorite international food?
• Are you a morning person or a night owl?
• What’s your favorite restaurant?
• How many siblings do you have?
• What would be your dream job?

• What would you do if had enough money to not need a job?
• Who is your favorite author?
• What was the last show you binge-watched?
• What TV series do you keep coming back to and re-watching?
• What hobbies would you like to get into if you had the time and money?

• If there was an Olympics for everyday activities, what activity would you have a good chance at winning a medal in?
• Did you participate in any sports as a child?
• Do you hang out with a large group of people?
• What is your favorite international food?
• What would your perfect vacation look like?

• Do you have any particular passion projects that you’re working on?
• Among your friends, what are you best known for?
• How do you spend a typical day?
• What’s the state of your social life?
• What music artist do you never get tired of?

• What are some accomplishments that you are really proud of?
• What are some obscure things that you are or were really into?
• What are some things everyone should try at least once?
• What fad did you never really understand?
• What is the aspect of dating that you hate the most?

• What’s the best thing that has happened to you this month?
• What would your perfect morning be like?
• Is there any art or artist you are really into?
• How many kids do you want in the future?
• What are you always game for?

• What do you do to unwind?
• What’s your favorite app on your phone?
• Cutest animal? Ugliest animal?
• Who is the kindest person you know?
• What’s your favorite piece of furniture you’ve ever owned?

• Who is your kind of people?
• What is the style of your ideal home?
• Where’s the strangest place you’ve ever been?
• What’s the silliest fear you have?
• What do you think a caterpillar would taste like?

• What would be the best city to live in?
• What household chore is just the worst?
• If you could give yourself a nickname, what nickname would you want people to call you?
• In a new relationship, what is one thing you are dying to try?
• What odd talent do you have?

• If you could give everyone just one piece of advice, what would it be?
• What would you like to know more about, but haven’t had the time to look into it?
• What do you normally do when you’re feeling shy and insecure?
• Do you like podcasts?
• What made you fall in love with one of your favorite musicians in the first place?

• What country do you never want to visit?
• What wrong assumptions do people make about you?
• Do you prefer to work in a team or alone?
• What has been the best period of your life so far?
• How have you changed from when you were in high school?

• How techie are you?
• What’s the most embarrassing thing you’ve ever looked up on Google?
• Will you prefer to live in a vending machine or be one?
• Which cartoon character do you think you most resemble?
• Where is the most fun place around where you live?

• Have you ever joined any meetup groups?
• Where would your friends or family be most surprised to find you?
• Have you ever had to remove someone from your life?
• Is there a food you don’t eat?
• What do you eat to make you feel better?

• When you were a child, what TV shows did you watch?
• What’s the most relaxing situation you could imagine?
• What is the most beautiful view you’ve seen?
• What is your favorite pastry to bake?
• What’s expensive but totally worth it?

• When do you feel most out of place?
• What’s the most recent thing you’ve done for the first time?
• How did you come to love one of your favorite musicians?
• What small seemingly insignificant decision had a massive impact on your life?
• How did you meet your best friend?

• Where would you move if you could move anywhere in the world and still find a job and maintain a reasonable standard of living?
• Would you like to be famous? (If yes, what would you want to be famous for? If no, why not?)
• What did you do last summer?
• What is one thing you will never wear outside?
• Do you believe your zodiac sign and birth chart describe you?

• If you lived to 100, would you rather keep the body or the mind of yourself at 30 until you were 100?
• Before you make a call, do you rehearse what you are going to say?
• What are you most grateful for?
• What’s the most essential part of a friendship?
• When was the last time you sang to yourself or to someone else?

• If you knew you were going to die in a year, what would you change about how you live?
• When was the last time you walked for more than an hour?
• What did you do for (the last holiday)? Or What will you do for (next closest holiday)?
• Best and worst flavor ice cream? What would make for an excellent new ice cream flavor?
• Who’s your favorite actor or actress?

• All modesty aside, what are you better at than 90% of people? It doesn’t have to be useful or serious, it can be something ridiculous.
• What’s the strangest phone conversation you’ve ever had?
• How much personal space do you need to be comfortable?
• What’s the most interesting fact you know?
• Do you have any tattoos? If so, what’s the meaning behind it?

• What fad or trend have you never been able to understand?
• Who’s your favorite character from a TV show, movie, or book?
• What TV shows did you watch when you were a kid?
• What do you like but are kind of embarrassed to admit?
• What’s your favorite smell?

• What skill or ability have you always wanted to learn?
• What’s the best meal you’ve ever had?
• If you could go back in time as an observer, no one could see you, and you couldn’t interact with anything, when would you want to go back?
• What’s the most amount of people you had to present something in front of?
• Where was your favorite place to go when you were a kid?

• What’s something that most people haven’t done, but you have?
• What says the most about a person?
• What machine or appliance in your house aggravates you the most?
• What places have you visited that exceeded your expectations?
• If you opened a business, what type of business would you start?

• What’s the worst movie you’ve ever seen?
• What’s the best road trip you’ve been on?
• What was the funniest injury you’ve ever suffered?
• How much do you wish you could simply set yourself on fire each day?
• Do you enjoy grocery shopping?

• How do you usually put on your toilet roll?
• What would peanut butter be called if it had a different name?
• If you found a briefcase filled with 1 million in $100 bills in front of your door, what would you do with it?
• What’s the worst advice someone has given you?
• Besides your home and your work, where do you spend most of your time?

• If you could have the answer to any one question, what question would you want the answer to?
• What are your top 3 favorite things to talk about?
• What do you care least about?
• Where would you like to retire?
• Who is the most bizarre person you’ve met?

• What are people often surprised to learn about you?
• Would you rather live full-time in an RV or full-time on a sailboat?
• What would you do with the extra time if you never had to sleep?
• When you were a kid, what seemed like the best thing about being a grown-up?
• What’s the strangest way you’ve become friends with someone?

• What’s your go-to series or movie when you want to watch something but can’t find anything to watch?
• What were some of the turning points in your life?
• What companies made you so mad that you would rather suffer bodily harm than give them more of your money?
• What small things brighten up your day when they happen?
• What sports would be funniest if the athletes had to be drunk while playing?

• What’s the most ridiculous thing you’ve done because you were bored?
• If you could send one letter to yourself in the past without the goal of making yourself rich (no lotto numbers, stock picks, etc.), what age would you choose and what would the letter say?
• How many other countries have you visited?
• What’s the name of your favorite band (not necessarily your favorite band)?
• What do you miss about life 10 or 20 years ago?

• How often do you dance? Silly/ironic dancing counts.
• What’s getting worse and worse as you get older? What’s getting better and better as you get older?
• Where’s the best place in (your town or city) to have a picnic?
• What’s your favorite thing to do outdoors? How about indoors?
• What’s your favorite holiday?

• What do you never get tired of?
• What habit do you wish you could start?
• What’s the best way to get to know who someone really is?
• What’s the last new thing you tried?
• Who besides your parents taught you the most about life?

• When are you the most “you” that you can be? In other words, when do you feel most like yourself?
• What’s the most spontaneous thing you’ve done?
• Have you ever texted a complete stranger just for fun?
• Why do banks have branches if money doesn’t grow on trees?
• Have you ever argued with your best friend over the same boy or girl?

• What would your nickname be if you were a boxer or a UFC fighter?
• How many times have you attempted telepathic communication with a dog just to see if you could?
• Could you survive without your phone for the rest of your life?
• What would you be if you had to be an item for a month?
• Are you currently accepting applications for a boyfriend/girlfriend?

• Have you ever spat in another person’s food?
• What’s the longest you’ve gone without picking up and consuming food that’s been dropped on the floor?
• What is the longest sleep you’ve ever had?
• What’s the best advice anyone ever gave you?
• What would you eat if you had to eat just one meal for the rest of your life until you became sick?

• Do you have any pet peeves?
• If we shouldn’t eat at night, why is there a light in the fridge?
• Would you rather eat a handful of bees or poison ivy?
• Where would you take me if you won a trip for two to anywhere in the world?
• What’s happening now, that in 20 years people will look back on and laugh about?

• How much social interaction is too much?
• How different do you act when you are with acquaintances vs. people you are comfortable with?
• On a weekend or holiday, what’s the best time of day and the best time of night?
• What are you looking forward to that’s happening soon?
• What really cheesy song do you love?

• What’s the worst or best job you’ve had?
• What’s been the most significant plot twist in your own life?
• Where did you take family vacations when you were younger?
• What’s your go-to funny story?
• If the company you work for / the college you go to had an honest slogan, what would it be?

• If you could instantly receive a Ph.D. in any discipline including all the knowledge and experience that goes along with it, what would your Ph.D. be in?
• How well do you cope when you don’t have your phone with you for an extended period of time?
• What were some of the happiest times of your life so far?
• Which Halloween costume is the most appropriate for your personality?
• How much longer are you going to sit in pain rather than get up and get a remote that’s out of reach?

• Have you ever been in a situation where you needed to make others laugh?
• Would you rather maintain your 18-year-old mind or body if you lived to 100?
• Would you rather have an incredibly fast car or incredibly fast internet speed?
• What are the top three social situations you try to avoid most?
• What friendship you’ve had has impacted you the most?

• What’s something you’re interested in that most people wouldn’t expect?
• What’s your favorite quote or saying?
• If you had the power to change one law, what law would you change?
• What’s the hardest you’ve worked for something?
• What is your favorite website?

• What took you way too long to figure out?
• If you could invent a new ice cream flavor, what would it be?
• Have you ever considered starting your own business?
• What’s your wish for me?
• Have you been to Disney World before?

• What is your most important goal right now?
• What are your thoughts on a partner who consumes alcohol on a daily basis?
• Can you describe a personal indulgence for which you would never apologize?
• When do you feel like you’re the most out of place?
• What are some of the little things that brighten your day or make you smile?

• Which member of your family do you have the most in common with?
• Do you like big parties or just small gatherings?
• How many times have you ever been in love?
• How do you feel about science vs. religion?
• Do you think you would be the type of person to settle down, or is that something that doesn’t really appeal to you?

• Do you ever bring your job home with you?
• What is the most important aspect of friendship?
• What is a piece of advice you often offer but find difficult to follow?
• What is that certain book that you’d love to see be made into a movie?
• How would you react if someone made you your favorite food?

• What are your top 5 favorite topics to talk about?
• What nicknames have you had throughout your life?
• What do you do differently than most people?
• Where’s the last place you’d ever go?
• What fact floored you when you heard it?

• How much-fried chicken do you enjoy?
• What abilities do you possess that will help you in surviving a zombie apocalypse?
• What do we all do as humans that seem to be ridiculous?
• Who is the best role model a person could have?
• If you unexpectedly won $10,000, what would you spend it on?

• What is the weirdest place you’ve ever been?
• Who would you like to swap places with if you could?
• How many donuts can you stuff into your mouth at the same time?
• What alcohol has a smell that reminds you of the night you almost died?
• Which animal do you think is the biggest party animal?

• What do you think am I thinking about right now?
• Have you set up a hidden code with a friend to get out of this date if things go wrong?
• How many days in a row do you wear the same pair of pants before it becomes a problem?
• Do you believe the cats are plotting against us?
• Why did Cinderella’s shoe fall off if it fit perfectly?

• If you only had 48 hours to live, what are the things you would do?
• How long does it take you to finish your bucket of popcorn during the first movie theater preview?
• What’s your Myers-Briggs personality type?
• What would be the perfect birthday present from someone who knew you well?
• What have you done in the last year that has forced you to step outside of your comfort zone?

• Do you celebrate your birthday? And, if so, in what way? If not, does it irritate you when others do it?
• What have you really wanted to learn more about but haven’t had the time?
• Do you agree with the outcome of any personality tests you’ve taken?
• If you had the time and money, what hobbies would you pursue?
• Can you tell me about something you’ve recently accomplished that you’re most proud of?

• What was a situation that you felt was bad at first but turned out to be a blessing in disguise?
• When was the last time you completed a task on your to-do list?
• Is there a documentary or book that has had a significant impact on the way you think about something?
• What New Year’s resolution would you like to keep?
• What do you believe people take the most for granted?

• Would you mind if I paid for both of our meals, or would you prefer that we each pay for our own?
• What is something you’re currently saving up for?
• Do you enjoy debating controversial topics?
• What is the first lesson you want to tell your children about love and relationships?
• What’s your favorite verse in the Bible?

• What is the priciest item you’ve ever purchased for yourself?
• What is something you would love to relive one day?
• Are there any decent movies out right now that you want to see?
• Do you consider yourself a calm or anxious person?
• What brings you the most fulfillment in life?

Do you have even more first-date questions? Share them in the comments so we can add them to the list!