Benjamin Otu EffiwattIf by chance you don’t know what a first date is, well here’s the formal definition according to Google: “the first of a series of social engagements between two people who have recently begun a relationship.” So…ya know. Fun! Date night.
While first dates are awesome, let’s be honest — they can also be a little stressful. You’re sitting across from some person your friend thought you’d click with, feeling the need to prove yourself interesting while also trying to determine if this human is actually your soulmate. And then there’s the small matter of conversation. When on your first date, what do you even say? It’s easy to fall into that predictable loop: “What do you do?” “Where are you from?” “Oh, I have siblings too! What about you?” It’s blah.
Why Asking Good Questions On A First Date Is So Important
I get it. You walk into a first date thinking about proving yourself and making a good impression. But here’s the thing. The person who asks interesting questions will always leave a better impression than the person who dominates the conversation by talking about themselves, or makes the dreaded, boring small talk.
Asking questions shows curiosity. Curiosity shows you care. When you ask someone something they didn’t expect you to ask — something that makes them pause and think before answering — you’re telling that person you want to know the real them.
Bonus: asking questions is also smart because you’re also trying to decide if you want to see this person again. Paying attention to what they say — and showing you care about what they say — can help you determine that a lot faster than simply talking about yourself.
12 Non-Boring Questions To Ask When On Your First Date
- What is something you are really proud of that most people would never guess about you? This question is golden because it gets them to share something personal about themselves that they aren’t already sharing. There is nothing quite like hearing someone open up about their true passions or greatest accomplishments. Their answer can teach you a lot about them, and opens the door for you to share something personal too.
- What does a perfect Saturday look like for you — no plans, no obligations, complete freedom? This question is low-pressure enough that it doesn’t come off like an interview, but open enough that they can share how they truly like to spend their time. Do they live for hiking? Are they always cooking up something crazy in the kitchen? Maybe they just relax all day and read a book. You’ll learn what they love to do off the clock, and what makes them tick.
- What is something you changed your mind about in the last year or two? Anyone can tell you what they do for a living. But how self-aware are they? How open-minded? This question allows you to get a glimpse into how they think. Maybe they used to hate yoga and are now a vegan mystic. Maybe they have changed their mind about a major life decision. Either way, you’ll learn what they value now versus before.
- Is there something you have always wanted to try but have not gotten around to yet? When people talk about things they want to do, you’ll notice their entire energy shift. They’ll light up because they are talking about something that makes them feel excited about life. Asking this question opens up a world of possibilities. You’ll learn what they’ve always dreamed of, and it also opens up some fun follow-up questions.
Have they always wanted to try it and never done it? Why not? What is holding them back? You’ll be surprised how far down the rabbit hole you’ll go just by asking.
- What is your relationship like with where you grew up? Do you feel connected to it, or did you totally outgrow it? You’ll be amazed how much someone can say about their upbringing when asked the right question. Rather than “Where are you from?” just dive deeper and ask them how they feel about it. Did they grow up loving it, or could they never wait to leave? Maybe they left and now love visiting; maybe they still don’t love it. This question unlocks all the feels.
- What kinds of things do you get truly excited about? (Not hobbies — but what really gets you psyched?) What do they love? What are they passionate about? I’m not asking about things they enjoy. I want to know what sets their soul on fire. The real stuff. You’ll be able to see their whole demeanor change when they start telling you about what they get passionate about. It’s also pretty cute watching someone get excited about something they love.
- Have you had any experiences that completely changed your perspective on life? Okay, this question is a little heavier than the others. But if your date is going well and you’ve both gotten fully comfortable with each other, I promise you’ll both enjoy answering this one. Some people have had amazing trips that opened their eyes. Others have fallen in and out of love. Whatever it is, they’ll tell you about that moment that changed their life and why — and that is pretty freaking cool.
- What is something you wish more people cared about? This question is subtle but sweet. Not only will you learn what they truly care about, but also how passionate they can get when something is important to them. Do they love animals? The environment? Politics? What makes them rage? You’ll learn a lot about their values by asking this question.
- Are you someone who makes new friends easily, or does it take a while for you to open up to people? This question is fun because you’ll learn what type of person they are when it comes to opening up to new people. And honestly, you’ll learn something about yourself when answering it too. Plus, people love talking about themselves. This is a win-win.
- What is the best advice you’ve ever received that actually stuck with you? This question rarely comes up on first dates, so not only will they appreciate that you asked something different, but they’ll have a lot of fun thinking about their answer — whether it’s life-changing advice they carry with them, or something silly that brightens up their day whenever they think about it. You’ll learn what they value by learning who they look up to.
- For you, what does connection feel like? If you’ve made it this far in the conversation and truly connected, this question will take you both somewhere real. You’re no longer asking about relationships. You’re asking them what it feels like to be truly connected to another person. Some will say friendship. Others will say being listened to. You’ll learn what meaningful relationships mean to them just by asking this question.
- What is something that will cheer you up no matter what your mood is? End the date on a fun, happy note. Something about asking this question makes people smile. When they tell you their answer, you’ll know exactly what makes them happy. And honestly? Knowing what makes someone else happy is one of the best pieces of information you can have about a person.
Tips For Great Conversation On A Date
Here’s the thing about asking great questions — if that’s all you do on a date, you’re going to seem a little intense. Yes, even with these questions.
When my now-boyfriend and I first started dating, I asked him questions all the time. Why? Because I was intrigued by him and wanted to know everything. It didn’t take long for him to tune me out.
Here’s how to actually use these questions to spark interesting conversation on your next date.
Listening is just as important as asking good questions.
Seriously. You’d be surprised how many people fail at this step. Ask open-ended questions, let the other person talk, and actually listen to what they are saying. If you’re wondering how to do that, here’s a quick guide.
-Don’t interview.
You don’t need to fire question after question. One good question can sustain a solid ten minutes of conversation if you let it. Learn how to listen, then throw out a question of your own that relates to what they just said.
-Answer your own questions.
This happens to me all the time. I ask someone personal, vulnerable questions and they’re too afraid to open up in return. Conversation is a two-way street. If you’re asking personal questions, be prepared to answer them too.
-Don’t force it.
Depending on your date, some of these questions may feel forced. If you feel like you’re pressing too hard, let it go. You’ll know when the conversation feels natural versus forced.
Conclusion
Listen, a first date doesn’t have to be a professional job interview, but it also doesn’t have to be some weird, forced party game where the two of you are pretending to be best friends who have known each other forever. If you show up to your next date with the intent to actually get to know the other person — and they do the same — you’re bound to have a great conversation.
These non-boring questions to start a conversation when on your first date aren’t hacks. There’s no trick. These are simply questions you don’t normally think to ask on a first date. But the beauty of asking questions others don’t ask is connecting with others on a deeper level. The real you.
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