There are few experiences as futile a rehashing the same ;canned, superficial questions in hopes of sparking a deeper, more meaningful conversation with someone.
Real insight into other people comes from authentic interactions. If your objective is getting to know someone better, it’s important to foster an environment in which you can both feel safe being your true selves during a candid, frank exchange.
And while it should be obvious, many of us forget that even the people we’re closest to or super interested in could use an invitation to open up further about themselves from time to time.
Asking well thought out questions is a way to cue that it’s OK for a guy to share more of himself, setting you apart from others in his social circle at any stage of your relationship.
Here are 20 good questions to ask a guy to get to know him better, whether you’ve just met or if you’re going on your 100th date.
1. What did your parents do while you were growing up?
Alright, this one is kind of sneaky because the real question here is “How is your relationship with your parents?” However, if things are strained there, he won’t want to answer that at all.
If you make the question about his personal backstory, he’s more inclined to gently let you know that this topic may be touchy than just to abrasively shut down.
2. What do you regret the most about [insert time of his life here]?
Drop this into conversation when he’s already talking about a time from his past to dig a little deeper and let him know you’re a safe space for discussing his shadows.
3. What’s the most recent thing that really turned you on?
This doesn’t have to be sexual! This can also pertain to art, music, a feat of engineering, a debate or something else that stimulated his senses and inspired him.
4. How does [recent event he’s discussing] make you feel, exactly?
This versatile question, when used correctly, not only lets you in a little deeper into his mind and motivations, but shows that you care about the parts of him that are more vulnerable and closed-off.
5. What’s your opinion of Jimmy Fallon?
“Don’t Trust the B. in Apartment 23” was right: Everyone has an opinion on Jimmy Fallon. And it’s important — crucial, even — to know if your opinion of Fallon meshes with his or you’ll never work out. Not ever.
6. What’s the worst thing you ever did as a kid?
Everybody got in major trouble with their parents at some point, but the real story here is how he remembers it and how he tells the story. Specifically, whether or not he’s able to laugh at or forgive himself years later.
7. What can I get you from the bodega/kitchen/beer shop/pharmacy/grocery store?
You can tell a lot about someone by how they ask for and accept help.
I’m not going to spout generalizations about the kind of person he must be based on what he requests, but noting his use of manners and gratitude are a sign that he’s an okay dude to be around.
8. Will you grab me a [thing you need] while you’re out, please?
Similar to #7, you can tell a lot about someone based on his willingness to help you out.
Just don’t treat him like your personal servant, obviously, and don’t let him do it to you, either.
9. Have you ever had a paranormal experience?
First of all, almost everyone has a story about something they’ve seen that they can’t explain, but even if he doesn’t, this is a great way to see what he believes in or doesn’t, how open minded he is about the unknown, and where he stands on conspiracy theories.
Plus, this kind of conversation usually makes for a good time.
10. Where did you learn to do [thing he enjoys doing or is good at]?
It’s one thing to listen to someone talk about thriving in their passions, but quite another to hear about the process of getting to the point of success.
Hearing about his mentors and the people he respects will give you incredible insight about his values and modus operandi.
11. Will you show me how you do [thing he’s better at than you are]?
First of all, there’s nothing sexier than watching someone fully in their element. Secondly, this is a great way to see how you work together and how he is able to acknowledge and work with someone else’s limitations.
A man who can instruct someone without being condescending or impatient is a man who is confident and capable in many, many other things.
12. What’s your least favorite book/movie/musician/artist/video game/sport?
It’s easy to ask about what someone loves, but you’ll learn much more if you ask what someone hates. Start small by asking about his feelings toward some inconsequential means of entertainment and if this conversation blossoms, it won’t carry as much weight or be as divisive as arguing politics or social issues.
All of this is a fantastic way to see how he handles gentle contradiction and his need to be right about things in general.
13. What’s the worst job you’ve ever had?
Everybody has a lousy job story which is a great thing to bond over; however, learning what he hated about it and the kind of flaws he sees and has conflict with in others gives a good sense of who he is in his social interactions away from you.
14. Have you ever lost anyone really important to you?
This is a touchy one, so it’s important not to pry here if you’re getting signals that he doesn’t want to talk about it any more than just a “Yeah” answer. However, if he offers more than that, go with it and take the time to learn about who this person was and why their life and death mattered to him.
15. I like your hat/haircut/tattoo/shirt/giant chrome belt buckle. Where did you get it?
Get him to talk about something he likes so much that he put it on his physical person and where he likes to look for things that express himself.
I particularly like to learn about people’s unique tattoos because there’s always an interesting backstory even if it’s not at all serious.
16. Why did you and ____ stop talking?
While this can be used for ex-girlfriends or estranged family members, it is important that you only use this when he’s already brought up a failed romantic or platonic relationship. You can’t just drop a cold “So why did your last relationship fall apart?” or “Why don’t you talk to your mom anymore?” on someone and expect a real answer.
If he doesn’t want to answer this, he doesn’t have to, which is also valuable information.
17. Why in the world do you support [problematic person]?
Here’s where things get a little heavier, but if you really want to get to know someone better, you owe it to yourself to at least listen to their perspective. And no matter how “woke” or principled he may be, every single one of us has, at some point or another, supported or admired someone who is problematic. (I know that because, at one point in all our lives, every human on this planet has been problematic to someone else.)
Understanding someone else’s opinion about the people he supports, backs, or admires lets you know what he values and is comfortable perpetuating, which may be a hard pill to swallow, but will shine a light on all his facets, including the ones you’re not compatible with.
18. Do you have any pets? Did you have any pets growing up?
It’s important to know how he feels about and treats animals. It just is.
19. What’s the most amazing thing you’ve experienced in the last few years?
It doesn’t matter how cool you think his social life is in this moment; it’s about learning what he thinks is cool and how it affected him.
If what he starts describing sounds like the lamest thing you’ve ever heard and you can’t bear listening to one more minute about it, refer to #4 and turn the conversation back to him.
20. What’s the worst injury you’ve ever sustained?
As with the rest of this list, this is not gender-specific. Everyone likes talking about battle wounds and, much like tattoos, scars have backstories.
Learning about a time someone was vulnerable, how he recovered, and his attitude about the whole thing now is an amazing insight about his attitude toward life in general.