Creating a connection comes down to one important thing: questions.
And it seems in this digital age, the art of conversation has been lost and we don’t know how to ask the right questions to really get to know someone. And that’s what dating is … it’s a discovery process. And the best way to discover someone and to assess how compatible you are, is through asking the right questions.
There’s a time and place for the right questions … a time to keep it light and a time to go deep.
This doesn’t mean you can’t ask serious questions when you’re first getting to know someone. There aren’t strict rules you have to follow because things like context and tone really matter. But you probably don’t want to pull out “When was the last time you cried?” on a first date (unless it somehow comes up naturally and you really get the vibe that he’s open to talking about it …)
Tone is key. Asking him “What is one thing you’re judgmental about?” can be either lighthearted or serious depending on the context, how it’s asked, and how he chooses to respond.
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Some questions can lend themselves to either a lighthearted or deep response, like “What is one thing no one realizes about you?” It’s up to him to be silly or serious, and that will tell you a lot about who he is, too. The point is, there is no formula that will tell you exactly what you can ask and when because so much depends on you, the guy, the timing, the context, the flow, etc. So what do you do when you can’t tell how receptive he is or feel uncertain about what to ask? One approach is to try asking progressively more serious questions and see how it goes.
How can you tell if you’ve gone too far? If he changes the subject he probably doesn’t like the direction you’re going. If he brushes off your question with a non-answer it probably wasn’t to his liking or it may have been too personal. Or if he’s answering with a lot of jokes, it could be a sign he’s uncomfortable with that level of intimacy and he’s trying to lighten things up. Be observant and respectful and don’t push too far if there’s not a good flow and you’re not having fun. And remember, you should be prepared to reciprocate by answering any question you ask! It’s a two-way street, and ideally, you’ll have a good back-and-forth that’s both easy and fun.
On that note, here are 28 fun, simple, lighthearted questions that will make you both smile and will help you learn a lot more about him.
1. What is something you always look forward to?
Concerts? Kisses? The weekend? Travel? Morning coffee? This question can have a million different answers, all fun and easy to talk about because it’s such a positive topic.
It can also tell you a lot about him without being intrusive. If he looks forward to vacation and travel, you’ll get to hear about his cool trips and where he wants to go next. Is he a beach or a mountain guy? Is his passport expired or just renewed? Or is he a homebody who prefers a staycation? This will give you a chance to see what you have in common.
2. What is a random thing that reveals a lot about a person?
Here’s a question that will tell you the kinds of things he notices and what he thinks is important. Answers are going to vary wildly and you’re probably going to be surprised. Does he notice if someone’s fingernails are clean and make much broader assumptions about that than maybe you would? Maybe he’s more keyed into personal hygiene than you realized. Or the random thing might be noticing whether or not someone’s got designer jeans on or expensive clothing in general and thinking that reveals a certain level of success. Maybe you agree or maybe you don’t, but it tells you something about him and his values.
3. What is a movie you watch over and over again?
A lot of us have that one movie that we can watch over and over and never get sick of. And it says a lot about a person what that movie is.
Does he like psychological thrillers? Humor? Mystery? Which characters does he love and which ones does he hate? This is a totally natural getting-to-know-you question that can tell you way more than surface information, and it leads to a low-key fun activity, watching your favorite flicks together!
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? This is a super fun question 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 a 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 favorite 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 here 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.
16. What is one thing that always cheers you up?
This is a lighthearted question that also gives you useful information and can lead to him sharing experiences with you about when someone’s cheered him up … or made things worse. Maybe he needs a hug when he’s down, or maybe he needs to be left alone. Some people are cheered up by little notes or being listened to.
17. The house is on fire, which three things do you grab?
This is a fun exercise that will also tell you his priorities. Does he save old family photos? His gun collection? His cat? Maybe his priority is not saving anything but the people in the house, because stuff doesn’t matter to him. Maybe you’ll learn he’s actually been in a house fire and had to make this decision in real life.
18. What is one thing you can never get enough of?
Is it sex? Beer? Bacon? Or is it accomplishing things in his career? His children? You never know what will come out of his mouth, but it might be what you least expect.
19. What is the best and worst part about being a guy?
This is an incredibly revealing question. Maybe he’ll tell you his man parts are very awkward and inconvenient at times, or that he hates constantly being asked to do the heavy lifting in every situation. You may learn that his favorite part about being a guy is that he loves traditional gender roles, being able to take care of a woman by opening doors and paying for things. Or this may be his worst part about being a guy! You never know.
20. Is there anything you’re superstitious about?
Is he all science and no superstition, or is he open to the idea that there are sometimes unknown factors driving things? Does he get uneasy if a black cat crosses his path or he walks under a ladder, even if he knows that’s ridiculous? Here’s where you learn if he’s uber rational or has a less logical and more open side to him.
21. Which do you prefer: a good book or a good movie?
This question can lead to so much more. If it’s a good book, when did he first start to love reading? What kind of books does he like? When does he like to read? And if it’s movies you’ll learn if he’s all action hero or sci-fi nerd or a little bit of both.
22. If you could be fluent in one language, what would it be and why?
This question will give you a chance to see what part of the world he’s interested in and why. Does he want to learn French so he can go to France on his next vacation, or Spanish because it will come in handy at work or in volunteering? Or maybe he wants to learn Farsi so he can read poetry in the original language. This question can lead to any number of answers depending on the guy you’re asking.
23. Have you ever dreamed of being famous?
Is he the kind of guy who’d like to be on “Love is Blind,” baring his soul to the world, or is he more introverted? Or maybe he’s interested in a different kind of fame—he wants to be an actor, or gain fame by doing something noble like contributing to the discovery of cures for incurable diseases.
24. What’s your biggest guilty pleasure?
What equals pleasure for him, and why is it guilty? Does he have a hard time picking among several guilty pleasures, or does he not believe there’s any such thing?
25. If you had three wishes, what would they be?
Is it money, fame, love? What would he do with them if he had them? Does he try to cheat and ask for more wishes? Will he share his wishes if you want one?
26. What is one subject you wish you knew more about?
This will tell you about his aspirations. Would he like to know more about flying so he can get his pilot’s license? More about what’s going on in the news and in the world so he can keep up when talking to people at parties? More about the line of work he’s in so he can advance in his career? Or more about some random hobby that’s just for fun?
27. What skill do you wish you could master?
Does he have a dream to learn knife throwing? A foreign language? Stand-up comedy? People are interesting and you never know what to expect. This can be a fun question to see both what his interests are, how he does or doesn’t work to achieve goals, and what’s important to him. He might talk about something he really sees himself mastering or he might talk about a far-fetched dream, and that will tell you something about who he is.
28. What is one temptation you can never resist?
Maybe he’ll tell you there’s nothing he can’t resist—he’s a paragon of virtue. Or maybe he’ll keep it light and tell you chocolate, or he’ll make it sexy and tell you lingerie. Or possibly he’ll tell you that when it’s fishing season and incredible weather he can’t resist playing hooky from work on Fridays to get away for the weekend with his buddies.
I hope this article gave you some fun and fresh ideas for questions to ask a guy to really develop a connection. Now I have a question for you. Do you know what inspires a man to commit to a woman? Do you know what makes him see you as a rare gem that he can’t let go of, a woman he wants to be with forever? If not, read this next: The #1 Things Men Desire in a Woman
And now another question. Do you feel like he might be losing interest? Does he seem to be pulling away? If so, you need to read this too: If He’s Pulling Away, Do This...