Fun Dating Questions

Whether it’s your first date or your thirtieth, you can always ask dating questions to get to know someone better. Try some general ones like these or choose a theme and let the conversation roll from there.

  • If you had one day left to live, what would you do?
  • Where would you most like to go on vacation?
  • What would you do if you won a million dollars?
  • What do you like best about me?
  • What one thing would you like to change about me?
  • Who was the first person you kissed?
  • How would you feel if I made more money than you?
  • Would you be willing to stay home with the kids while I work?
  • What is the craziest dream you’ve ever had?
  • If you could trade lives with someone, who would it be?
  • What’s one thing no one knows about you?
  • Would you rather go for a hot air balloon ride or bungee jump?
  • What’s the strangest thing you’ve ever eaten?
  • If you could ask me anything and have me answer truthfully, what would it be?
  • What keeps you up at night? Or do you go to bed at a reasonable time and go right to sleep with no problems?

 

Future Dreams and Career Choices

Knowing a potential boyfriend or girlfriend’s future goals will let you know if you’re on similar paths and whether you’re compatible. It’s also fun to ask dating questions that compare where someone thought they would be at this age to where they actually are now.

  • What did you want to be when you grew up?
  • What are three things on your bucket list?
  • If you could choose any career right now, what would it be?
  • When you were a kid, did you think any dream career choice was out of reach? What was it?
  • What was the first major you declared in college?
  • What do you see yourself doing after retirement?
  • If money didn’t matter, what would you do with your time?
  • If you had to choose a career you loved for little money or choose one you didn’t enjoy for a high salary – and commit to it for five years – which would you pick?

 

 

Potentially Embarrassing

Before you launch into dating questions that could potentially have embarrassing answers, gauge how the other person is feeling. Are they the type of person who’s likely to be an open book with their answers and willing to laugh them off with you, or are they more guarded and probably worried about sharing too much? If you’re relaxed together, feel free to ask these dating questions and share a few good laughs. You should be willing to answer dating questions too, just to keep things fair.

  • What is your most embarrassing moment?
  • What is something you did as a child your parents don’t know about?
  • What do you think is the dumbest thing you’ve ever done?
  • Is there a silly accomplishment you’ve made that you’re secretly proud of?
  • What’s a silly habit you have now that you don’t tell a lot of people about?

 

 

Favorites

You could set this up as a game and ask each other as many “favorites” type questions as possible within an allotted amount of time. Asking someone what their favorite things are, will give you a lot of information in a short amount of time, and it usually won’t feel like you’re prying (especially if you are both answering the dating questions). You can also get ideas for future date activities.

  • Who is your favorite movie star?
  • What’s your favorite kind of food?
  • What’s your favorite outdoor activity?
  • What’s your favorite book?
  • What’s your favorite time of day and why?
  • Who is your favorite superhero?
  • What is your favorite color?
  • What is your favorite season?
  • What is your favorite restaurant?
  • What is your favorite sport to watch? To play?
  • What is your favorite thing to write or draw with?

 

Media and Today’s Culture

From pop culture and phone apps to old favorites and magazine subscriptions, learning about a person’s media preferences can give you insight into who they are early in a relationship. During the first couple of dating questions like these may feel more comfortable than some other types.

  • If you could pick any character from a TV show and pair them with any character from a book for a whole new story, who would you put together?
  • What phone apps are you obsessed with?
  • Would you rather give up music or television for a month?
  • Which magazines do you subscribe to?
  • Is there a show you used to watch as a kid that you would love to see come back?
  • Which movie do you most regret wasting two hours of your life on?
  • If you could meet any band, past or present, which one would it be?
  • What’s a word or phrase people use that you just can’t stand?
  • How do you feel about emojis and abbreviated words (like “u” instead of “you”) in texts and emails?
  • Have you ever gotten revenge in a silly way on someone who hurt you (a prank, for example)? What did they do and what did you do?

 

 

Personality and Fun Facts

People love talking about themselves and sharing little tidbits that make them feel unique. Ask these, then sit back and listen. Be prepared to answer them, too.

  • How do you handle it when your family doesn’t approve of a decision you’ve made?
  • What song can always make you dance, especially when no one’s around?
  • Do you sing in the shower?
  • Do you have any odd quirks?
  • Do you have any hidden talents?
  • Do you read your horoscope? Do you do it for fun or do you take it seriously?
  • Do you consider yourself an old soul?
  • How do you feel about crowds of people?
  • Do you hold grudges or forgive easily?
  • Do you like when people give you gifts, or does it make you feel awkward?
  • If you had to wear one outfit from head to toe every day for a year, what would it be? (You could have more than one of each item so you could wash them and they wouldn’t wear out before the year was done, but you’d have to look the same every day.)

 

 

Ask Away

Obviously, certain questions are appropriate for different phases of a relationship. You wouldn’t want to ask someone on the second date to reveal to you what most people don’t know about him, but you may be able to if you’ve been together for several months. Some dating questions that will be perfect for anything from a casual date to date #102 with your boyfriend.

 

Use your judgment when it comes to asking questions, and you’ll feel as if you know each other in record time. Questions like these – as well as a couple of serious ones – are good to have in mind on dates because they keep the conversation lighthearted, keep it moving, and most importantly, they keep it fun.

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Fun Dating Questions
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