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100+ Cute, Funny, and Interesting Questions to Ask Your Boyfriend or Girlfriend

It can be hard to find things to talk about in a relationship, especially if you haven’t been dating for very long. The following questions make great conversation starters, and they range from silly and cute to deep and thought-provoking. The questions also don’t assume the gender of the asker, so there aren’t typical questions like, “what is your favorite makeup look on me” or “what is your favorite dress,” which makes this list friendly to both straight and same-sex couples.

Everyone's favorite dating questions are about love and romance.

Everyone's favorite dating questions are about love and romance.

Love, Romance, and Sappy Stuff

  1. What was your first kiss like? If you haven’t had it yet, what do you expect it to be like?
  2. Do you believe in love at first sight? Have you ever experienced it?
  3. Have you ever been in love? How many times?
  4. What is most important in a partner—intelligence, appearance, or compassion?
  5. What is your ideal first date? Give as much detail as you can.
  6. What is the worst date you’ve ever been on? Did you ever go on another date with that person?
  7. What qualities do you want in a potential spouse?
  8. What was our first kiss like? Is our last kiss better than our first?
  9. Where is the most romantic place you can think of?
  10. Would you rather spend a day cuddled into bed with me or spend it exploring a new city?
  11. What is a more attractive quality in a partner, common interests or a shared sense of humor?
  12. How long do you have to know someone before you know you're in love?
Gaming, movies, and TV shows are all forms of entertainment to ask your boyfriend or girlfriend about.

Gaming, movies, and TV shows are all forms of entertainment to ask your boyfriend or girlfriend about.


  1. Do you like video games that have guns and war or magic and fantasy? If you don’t like either, what kind of games do you like to play?
  2. Do you prefer to play sports or watch them? Which ones, and if you don’t like to do either, what is something you like to do instead?
  3. What is your favorite TV show? If you don’t watch TV, what else do you do to kill time?
  4. Do you prefer to watch movies, TV shows, cartoons, or anime?
  5. What is your favorite movie? When is the first time you saw it? Would you watch it again - with me?
  6. What was your favorite book growing up? If you didn’t like to read, what other things did you like to do?
  7. What is the worst video game you have ever played? Did you like it anyway?
  8. What is your favorite hobby?
  9. Would you rather go to a convention (like MomoCon or ComiCon) or go to a regional festival?
  10. Do you prefer playing creative games that let you design and build things or strategy games that let you compete?
  11. Do you ever let other people win games or do you always do your best?
  12. What's a movie you could watch over and over?


  1. Do you like to cook or bake? If you do, what is your specialty?
  2. What is one food you could never give up?
  3. Could you be a vegetarian? Vegan? If you are a vegetarian or vegan, what made you decide to not eat animal products?
  4. Have you ever ate a specific food so much you ruined it for yourself? If you have, what was it?
  5. What is your favorite food to have on your birthday?
  6. If you could only eat food for the rest of forever, what food would you choose?
  7. What is the worst food you have ever tried? Did you expect it to be that bad?
  8. Do you prefer burgers or pizza?
  9. Do you prefer waffles or pancakes?
  10. Do you prefer mashed potatoes or french fries?
  11. Do you prefer Chinese food or Mexican food?
  12. Do you prefer sweet or salty foods?
  13. Do you prefer tea or coffee?


  1. Do you like to travel or are you more of a homebody?
  2. Would you rather travel long distances by car, bus, plane, train, or boat?
  3. Have you ever been on a plane? Did you like it?
  4. Have you ever been on a train? If so, did you like it?
  5. If you could travel to any country in the world for an all-expenses-paid summer vacation, where would you go?
  6. Would you rather live in the city with lots of people or by yourself in the countryside?
  7. How far north have you traveled? How far south? East? West?
  8. Where is the most beautiful place you have ever been?
  9. Where are three places you want to visit before you die?
  10. Would you rather go somewhere with a lot of historic significance or somewhere with a big amusement park?
  11. Would you rather go to an art history museum or a natural history museum?

School Daze

  1. When you had projects in school classes, did you organize the group, do the artwork/handwriting, do the research, or let everyone else do the work and just write your name on the paper?
  2. Did you enjoy art and music classes, or did you prefer more traditional classes like history, math, literature, and science?
  3. Did you ever have a crush on a teacher? What made you like him or her?
  4. What is a class you always wanted your school to offer but never had a chance to take?
  5. If you could afford to take classes at a community college just to learn new skills or knowledge, but not get a degree, would you do it? If you would, what kinds of classes do you think you would be interested in?
  6. What was the most boring thing you learned about in school? Did you ever use the information?
  7. Would you rather write a five-page essay and not have to read it aloud or present a one-page speech that you wrote to a class?
  8. What do you think is more interesting, hard sciences like chemistry and physics, or soft sciences like psychology and sociology?
  9. How much education do you already have? How far would you like to go?
  10. Is there a university or school you’ve always wanted to go to?
  11. Have you ever wanted to do a study abroad program?
  12. If money were no object, how much education would get?
  13. If money were no object, what degree what would you get?

Flirty Questions

  1. Do you like to cuddle?
  2. Are you big spoon or little spoon?
  3. What was the first thing you noticed about me?
  4. What qualities do you like in me the most?
  5. How can you tell you're in love?


  1. Do you ever feel like you were “born in the wrong decade”? Would you have rather lived in another time in history?
  2. Do you procrastinate or do you do get everything done early?
  3. How organized would you say you are? Do you wish you were more organized, or do you like a little bit of clutter?
  4. Have you ever had a pen pal? Have you ever wanted to?
  5. What is your favorite kind of pet? Have you ever had one? If you don’t like animals, what is wrong with you? (The last question is optional.)
  6. Do you believe in astrology? What is your zodiac sign?
  7. Have you ever had a handwriting personality test done, either for fun or professionally?
  8. Would you rather work really hard and retire at 40 or work at your own pace and never retire?


  1. What is your favorite cologne or perfume? How long have you worn it?
  2. What is the longest your hair has ever been? Why did you get it cut?
  3. What is the shortest your hair has ever been? Why did you grow it out?
  4. Do you have any tattoos? What do they mean to you? If you don’t have any, would you ever get any?
  5. How would you describe your fashion style? Do you put a lot of work in your appearance?
  6. Is it more important to you that you are comfortable or that you look good?

Family Matters

  1. What family member were you closest to growing up?
  2. Do you like kids? Do you have a favorite age range that you like to spend time with the most?
  3. What is your favorite family tradition? Do you still carry it on?
  4. Do you ever wish you had more/less brothers or sisters? Do you think you have the perfect amount?
  5. What do you think is more important in a family member, honesty or kindness?
  6. If you could teach your own children only one lesson, what would it be?
  7. Do you want your own children? If so, how many?
  8. Would you ever adopt?
  9. Would you ever foster?
  10. How important is it to visit your family at the holidays?

The Deep Stuff

  1. Do you believe in life after death? If so, what do you think it will be like?
  2. Do you believe in reincarnation? If you do, what do you think happened in your past lives? What do you think will happen in your future ones?
  3. If you ever got married and it didn’t work out, would you get married again? What about if you were widowed?
  4. What is the most important current political issue to you right now? Could you be with someone who doesn't agree with you on this?

Works Cited

Daily, Lisa. “Dating Averages: What’s Your Normal?” September 18, 2009. Accessed: December 29, 2009.

Evans, David. “ Success Rate.” Online Dating Insider. Accessed: December 29, 2009.

Spindel, Janis. How to Date Men: Dating Secrets from America’s Top Matchmaker. New York, NY: Penguin Group, 2007.

Did you ask these questions and get some unexpected answers? Let me know in the comments below!

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2018 Dani Merrier