1. WHAT’S SOMETHING YOU’RE GLAD YOU’LL NEVER HAVE TO DO AGAIN?
This questions can be very telling. Usually the experiences we never want to do again were the hardest, but also the most transformative, the ones that helped shape who we are. Usually the worst things we go through in life are the things that make us realize how strong we are.
2. WHAT’S ONE THING YOU ALWAYS PROCRASTINATE ON?
This is a good question to see how grounded and efficient someone is. There’s always a reason why we procrastinate on something, but we don’t always immediately know why. People who are more floaty types will usually procrastinate on practical, day-to-day tasks while people who are more Type-A and goal-oriented will have a hard time with feeling-tasks.
3. WHAT WOULD YOU DO WITH YOUR LIFE IF YOU WERE SUDDENLY AWARDED A BILLION DOLLARS?
questions-to-ask-a-guyWe all pretty much work to live and while you might enjoy your job very much, it might not be the thing you would choose to do if you didn’t have any bills to pay. This question is telling because it shows what someone values in life and what their deepest desires are. Do they want to travel the world? Dedicate their life to charity? Teach underprivileged kids? (These are actually some of the responses I’ve gotten to this question on dates!)
4. WHAT SHOULD A HEALTHY RELATIONSHIP PROVIDE FOR THE PEOPLE IN IT?
Everyone has different needs in a relationship, they have things they are able to give and things they want to receive. People usually give love in the way they most feel loved, but not everyone experiences love in the same way. When you and your partner complement each other in terms of what you each want to give and get, having a loving, healthy relationship will be pretty seamless. If you have different needs, then you might need to work a little harder to each person is satisfied. Either way, this is a great question to gain an understanding of how he views relationships.
5. DO YOU BELIEVE EVERYTHING HAPPENS FOR A REASON, OR DO WE JUST FIND REASONS AFTER THINGS HAPPEN?
Most people are divided into two categories, the ones that thing everything is destiny and the ones that think life is a series of random occurrences. This thought provoking question will give you insight into where he stands and is sure to rouse some very interesting conversation.
6. IS THERE ANYTHING YOU CONSIDER ABSOLUTELY UNFORGIVABLE?
Someone’s answer to this question will probably depend on their life experiences, for instance, if they’ve been cheated on and now consider that unforgivable. Some people can forgive anything, others are pretty tough and may have a low threshold for certain behaviors.
7. IF YOU WOKE UP TOMORROW WITH NO FEAR, WHAT WOULD YOU DO FIRST?
Now wouldn’t that be a fun thing to wake up to! Use this fun question to figure out what he really wants to do in life, and what’s holding him back from getting there.
8. IN YOUR LIFE, WHAT HAS BEEN THE BIGGEST BLESSING IN DISGUISE?
We’ve all had experiences that felt like the worst possible thing that could happen at the time and ended up being one of the best things to ever happen, and it can be fun to look back and see that a lot of the time, things do work out for the best.
9. IF YOU COULD PICK ONE YEAR OF YOUR LIFE TO DO-OVER, WHICH WOULD IT BE AND WHY?
People can interpret this question in different ways. Some might want to re-live a year that was really fun and amazing and others might want a re-do of a year where they made significant mistakes. Either way, it’s fun to think about.
10. WHAT IS ONE BEHAVIOR THAT YOU NEVER TOLERATE?
Everyone has their personality pet peeves, guys in particular can get very turned off (even if they’re out with a supermodel) but certain behaviors that they find completely unattractive. When you ask him this question, you’ll learn his deal breakers (hopefully) before you commit any of them!
11. DOES SPENDING TIME WITH OTHER PEOPLE ENERGIZE YOU OR DRAIN YOU?
This question will tell you if he’s an introvert or extrovert. A lot of people think it’s easy to distinguish between the two but it’s not. People assume extroverts are fun and friendly and chatty while introverts are shy, withdrawn, and quiet. This mistake is the reason why I thought I was an extrovert my entire life when really, I’m an outgoing introvert! Extroverts usually feel energized by being around people while introverts need time alone in order to re-charge.
12. IF YOU COULD WRITE A NOTE TO YOUR YOUNGER SELF, WHAT WOULD YOU SAY IN ONLY THREE WORDS?
This question is both sad and sweet, because don’t we all wish we could impart some wisdom onto our younger selves? It also has the potential to talk a bit about your childhoods, which is a really significant way to get to know someone since so much of who we are was shaped in our early years.
13. WHAT IS THE ONE THING THAT MAKES YOU FEEL ALIVE?
We all have something. Men in particular need to feel like they are achieving their “mission” in life. Every man has one, but not all of them are actively working to achieve it. His mission is usually the closest thing to his heart, the thing that makes him feel alive. This question will give you insight into what his mission is, which will tell you a lot about who he really is.
14. WHAT WOULD YOUR PERFECT DAY LOOK LIKE?
It doesn’t have to be a special day (although he might interpret this question that way, like my husband who answered, “our wedding day”), it can be his perfect ordinary day. What time he wakes up, what he does, who he sees, what he accomplishes. This will show you what makes him feel good and on top of the world. We all have those days where everything clicks and everything feels right and they’re the best! This is a great way to find out what his looks like.
15. IS SOCIAL MEDIA BRINGING US CLOSER OR MAKING EVERYONE MORE ISOLATED AND ALONE?
This is just a great conversation starter because you can easily argue both sides. It’s not as personal as the others, but it’s a fun thing to talk about and a great ice breaker if you’re in the early dating phases.
16. DO YOU USUALLY FOLLOW YOUR HEAD OR YOUR HEART WHEN MAKING DECISIONS?
This one will reveal if he’s a thinker or a feeler. Most people will answer both, but try to encourage him to choose the one that he follows most of the time. Most people have a primary mode of making decisions, either they go by how they feel or they go by logic.
17. WHEN IS THE LAST TIME YOU CRIED?
Even the manliest men go soft sometimes. Try to see if you can get an honest answer out of him, just make sure to make him feel safe sharing it with you and won’t feel like you’ll make fun of him or think he’s less of a man.
18. WHAT IS YOUR ALL TIME FAVORITE BOOK?
Everyone has that one book that is barely even glued together anymore because they’ve read it so many times. And these books are our favorites because they resonate with us on a personal level. Find out what his favorite is and why.
19. WHAT IS SOMETHING THAT NEVER ENDS WELL?
This question can have so many answers, from something serious to silly, have fun with it!
20. WHAT’S THE BEST WAY TO END A LONG DAY?
This question is another easy and fun one, if you’re doing these in order it will be a nice respite from all the deep and heavy ones! Getting to know someone is about learning who they are (what they value, what their personality traits are, how they feel about things), and what they like and enjoy and this question is a good way to learn about the latter.