4. What is something you’re embarrassingly bad at?
Does he have a sense of humor and can he laugh at himself? Is he okay with looking a little silly in your eyes? These are super fun questions to ask a guy that also requires a bit of vulnerability.
5. What is your spirit animal?
Again, a super lighthearted question that can also tell you a lot. This is a fun and revealing question that encourages him to take of his “mask” and show you the real him without actually talking about himself. Is he an eagle or a bear or a dog? Does he joke that he’s a weasel? (Watch out! People tell you who they are…)
Ask him what he has in common with his spirit animals, what qualities he shares with them.
6. If you could only eat three foods for the rest of your life, what would it be?
This won’t just tell you his favorite foods, it will tell you about his priorities. Would he eat ice cream, potato chips, and beer for the rest of his life, or is he health-conscious enough to think about the actual effects of that kind of diet?
Does he go in the opposite, totally healthy direction with fish, broccoli, and whole grains? Or does he take a balanced approach with two healthy foods and one treat? Maybe you learn that coffee is really, really important to him, or that he can’t live without cheese.
7. What topic do you have a lot of useless knowledge in?
People love to share what they know! If it’s about something random or useless, it’s bound to be hilarious. Was his last read about the history of lawns in America? Why does he know so much about lawns? This question will open the gates for a lot of fun conversations.
8. What is something that never ends well?
You’re going to get some funny stories with this question. If he’s drawing a blank, help him along by adding to it. What is something that never ends well in college? At work? In a relationship?
9. What are people always surprised to discover about you?
This is another chance for him to take off his “mask” and be the real him with you. People conform in life, but everyone wants to be unique, and he’s going to want to show you why he’s different from everyone else.
What quirk does he have that he thinks is unusual or that you won’t expect? Is he willing to share it with you? This gets at the disparity between how people see themselves, how other people see them, and how they think others see them—three layers to explore.
10. What is your favorite part of the day?
Is he night owl, relishing time alone when everyone else is asleep? Or does he love an early morning walk with his dog and a cup of coffee? Maybe he loves having a drink after work, or if he’s especially career-driven, maybe the favourite part of his day is starting work and knocking stuff out. His answer can reveal a lot about what he enjoys most and who he is.
11. What is something that happened to you that’s so absurd you wouldn’t have believed it if you weren’t there?
More fun stories! Hearing how he responded to the absurdity in the moment and how he views it now will be telling, as will what he thinks is absurd. Maybe his threshold is higher or lower than yours, or maybe it’s exactly the same.
12. Do you believe in zodiac signs?
If so, what in your zodiac is true and what’s not? If he’s a Taurus is he stubborn and sensual? If he’s a Libra is he well-balanced and charismatic? If he believes Zodiac signs are accurate this will tell you how he sees himself. If he knows a lot about it, ask him to tell you about your sign. And if he doesn’t believe zodiac signs are accurate, ask him why.
13. What is one story you tell that always makes people laugh?
This gives him a huge opening to make you laugh … and men love to make you laugh!
14. Do you believe in past lives?
This is one of the fun questions to ask a guy that will give you an idea how openminded he is. As with so many of these questions, the fun part is getting into the “why” he answers a certain way and what kinds of stories he has to share.
15. When was the last time you used YOLO as an excuse to do something?
And what did you do? This is a chance to learn about his adventures, or to learn that he doesn’t really have an adventurous side. Maybe he needs someone in his life to show him YOLO.
Just because someone doesn’t have a particular character trait that you might admire doesn’t mean they aren’t open to it. We all bring different strengths to the table in a relationship, so don’t assume that his answers or lack of them is a sign that he’s missing something; it could be that it’s there and just needs to be drawn out a little.