Fun Relationship Questions

Crystal Schwanke
couple on a date

When you're first getting to know someone, a lull in the conversation can feel awkward. With fun questions to ask, you won't have to wonder what to say. Just ask a few and get the conversation rolling again. You'll learn a lot more about each other than you would taking in another movie, and a list of fun questions is great to have on hand for a coffee or dinner date, just in case.

Fun Questions for Your Next Date

  • 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 $10,000?
  • What is your most embarrassing moment?
  • Who is your favorite movie star (of the opposite sex)?
  • What do you like best about me?
  • What one thing would you like to change about me?
  • Who was the first person you kissed?
  • What is something you did as a child that your parents don't know about?
  • Role questions. Examples of this type of question include "how would you feel if I made more money than you" and "would you be willing to stay home with the kids while I work?"
  • What is your favorite color?
  • What is your favorite season?
  • What is your favorite restaurant?
  • What is the craziest dream you've ever had?
  • What do you think is the dumbest thing you've ever done?
  • Is there a silly accomplishment you've made that you're secretly really proud of?
  • If you could trade lives with someone, who would it be?
  • What's your favorite time of day and why?
  • Who is your favorite superhero?
  • Is there a show that you used to watch as a kid that you would love to see come back?
  • What's your favorite outdoor activity?
  • What's your favorite book?
  • Which magazines do you subscribe to?
  • What's one thing that almost no one knows about you?
  • Would you rather go for a hot air balloon ride or bungee jump?
  • Would you rather give up music or television for a month?
  • What are three things on your bucket list?
  • What's your favorite kind of food?
  • 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?
  • What's the strangest thing you've ever eaten?
  • Do you have any odd quirks?
  • What did you want to be when you grew up?
  • If you could choose any career right now, what would it be?
  • Do you have any hidden talents?
  • What phone apps are you obsessed with?
  • 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?

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. There are some questions that will be perfect for anything from a casual date to date #455 with your boyfriend, however. Use your judgment when it comes to asking questions, and you'll feel as if you know each other very well 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.

Fun Relationship Questions