45 Fun Questions To Ask On Your Next Date

Let's be honest, dating is not always fun. While it can be exciting to meet someone, the first few dates with different people can feel like the same thing over and over. You go have dinner or somewhere standard and ask the same, expected questions. But you should not have to dread your next date – dating should be fun! So, if you have a date coming up and are dreading the lull in the conversation when the chemistry just does not seem to be flowing, here are some fun questions you should ask. Some of these questions are just silly and may not actually help you get to know the essentials about your date. But then again, even the most unconventional questions have answers that will shed some light onto your date’s personality. Otherwise, these questions will help break the ice and show you and your dates’ senses of humor, which essentially helps you two feel more comfortable around each other.

#1. Cats or dogs? ~The age-old question. #2. If you could get your clothes from one store for the rest of your life, from where would they be? ~This fun question could surprisingly tell you a lot about your date. You will learn their preferred style, such as if they favor comfortable or athletic clothes or well-dressed outfits. Their choice will also give insight into how they spend their money. Do they shop at cheaper stores with a wider variety or prefer higher quality? #3. When is the last time you took a bath? ~Nowadays, most people shower. But baths offer great benefits for relaxing. Find out if and how your date takes the time to unwind. #4. Favorite flavor ice cream? ~They say a person’s favorite ice cream says a lot about their personality. Who knows if this is actually valid. Find out on your next date! #5. What is your least favorite type of food? ~Food compatibility is actually pretty important in relationships. If you always want sushi or Chinese but your date is more of a pizza and hamburger person, your nights out together might get complicated. Figure it out now. #6. Earl gray or jasmine? ~Tea lovers unite. #7. Are you a morning or night person? ~Find out if your next date with this guy will be a morning hike or a night out on the town. #8. What is your favorite alcohol? ~A fun way to ask if your date wants another round of drinks. #9. Would you rather go to a concert or to the theatre?

#10/ AIM is shutting down soon – what was/were your screennames? ~Let the embarrassment commence. #11. How did you meet your current best friend? #12. What were some of the talents with which you entered into talent shows as a kid? ~Find out what they liked to do (or what their parents forced them to do) as a child. #13. What was/were all of your majors in college? ~You can follow up with what their favorite class was at school or if they had any outstanding professors. #14. How often do you clean your home? ~Find out here if your date is really type-A or a germ-freak. #15. What were all of the jobs you, at a point in your life, saw yourself becoming? ~Let your date take a trip down memory lane while you get a sneak at what has motivated them throughout their life. #16. Where is your favorite spot in the world that you head to when you want to relax and unwind? ~Give your date as long as they want to answer this question, especially if they have a few answers! Like the bath question, this one can tell you how they relax, what calms their soul and helps them unwind. For some, this might be their bed playing a video game. For others, it might be at the park or a bookstore. Really, any answer will give insight into their personality. #17. What is the one thing you want to know about me? ~This is an especially fun question if you have already had several dates or regularly see this guy.

#18. Do you have a hidden talent? #19. Which sport do you wish you were so good at that you could enter the Olympics? #20. Would you ever climb the Half Dome at Yosemite? ~A perfect question to venture into a conversation about their likes and dislikes of nature and the outdoors. #21. Which holiday do you get the most excited for? ~Superficially, this question is fun. But it also gives you the chance to find out something deeper about your date. Holidays speak to their family, their social life, and even their ethics. Find out what is important to your date. #22. Which actor would play you in a movie of your life? ~Ah, a good question to see what your date thinks of themselves. Potentially fun, potentially mischievous. #23. What is your favorite/spirit animal? ~This question is not the most unique, but it is another fun and gentle one to help you better understand what this guy thinks of himself. #24. Which website do you visit most frequently? ~It might be better to not include Facebook, Netflix, e-mail accounts, and other social media platforms, since these will probably be the majority of people’s answers. Instead, look for what your date does or searches for on the internet. Do they watch a lot of videos on YouTube, check out tech websites, or follow a news platform? #25. What is your favorite thing about not being in a relationship? ~This question calls for a mature answer. You might even hear something you do not want to. Regardless, you are bound to learn a bit more about your date’s psyche with this question. ~For example, if you have been seeing this person for a while now, then you will learn any hesitations they have about the next step of your relationship with them or what they will still want once you two become serious. ~If this is an early date, then this question might help you understand why your date is still single. #26. What is a bad habit you have and would like to change?

#27. If you had the opportunity to write something at any length, what would it be (about) and where would you want it published? ~Here, you can find out what is important to your date or what motivates them enough to want to share with others. #28. For whom did you vote? ~A rather good question if you are looking for a potentially heated or passionate conversation, no matter your date’s answer. Another way to phrase it would be, “What did you think about the election?” #29. Do you think aliens are real? ~Other options include mermaids or Big Foot. #30. Which news outlet or magazine do you subscribe to/have on your phone? #31. Should menstruation products be made free? ~Be bold, ladies. #32. Your thoughts on Vegetarianism? ~As a passionate vegetarian myself, this question always tells me if the person is worth a second date. #33. Do you use the Oxford comma? ~I am not sure how someone could lead into this question on a date, since it is not very casual. Take your date by surprise and ask it out of nowhere.

#34. Which languages do you know or would want to learn? ~This question opens so many doors for conversation. You could subsequently ask about why your date learned a certain language. You can learn to which countries they have travelled. If your date wants to learn another language, they will probably have a reason, like wanting to read something in its original language or wanting to travel somewhere else. Find out why! #35. What impressed you most about the best place to where you have travelled? ~When asking this question, do not settle for hearing what this guy's best vacation was because the resort was nice or the weather was perfect. You do not actually care that the hotel in Paris looked out over the Eiffel Tower or the beach in Bermuda was beautiful. Challenge your date into their cultural knowledge of the places to which they have travelled. #36. What’s your number (AKA how many people have you been with?) ~This questions is perhaps not first date material. It also might not be something you want to know. But this question could be a fun way to discover more about your date’s self-esteem and their relationship with their sexuality. #37. When did you read your favorite book? ~Asking what is their favorite book is a very typical first date question. Instead, ask your date when and why they read it. Was it for school, for a book club, or for fun? In this way, you can find out what form reading takes in their life.

#38. What’s the difference between a beer and lager? ~Bonus points if you ask this when your date is a total bust and you have nothing else to talk about. #39. Do you think Hermione and Harry should have actually ended up together? #40. Does your birthday sign match with your personality? #41. Red Sox or Yankees? ~Or some variation of the teams of where you’re from. #42. Who is your favorite superhero and why? ~Follow up question: which superpower do you wish you had? #43. Which house in Game of Thrones would you want to be a part of? ~If your date says that they don’t watch the show, then your date next could be a TV marathon. #44. Which character do you pick when you play Mario Kart/Mario Party?

#45. Where will you take me on our next date? ;)