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 he 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 icebreaker if you’re in the early dating phases.
16. Do you usually follow your head or your heart when making decisions?
When you ask these sorts of questions to a guy, it 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 the 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.
So there you have it. My all-time favorite questions to ask a guy to get closer. I tested all of them out on my husband and we had a lot of fun with them and I hope you do too. Give them a try and leave me a comment letting me know how it went!
Written by: Sabrina Alexis
Originally appeared on: A New Mode
Republished with permission.