30 fun and engaging questions to ask on a first date
Clinically reviewed by Dr. Chris Mosunic, PhD, RD, CDCES, MBA
First dates can be cringey, but it doesn’t have to be that way! Here are 30 engaging questions to ask on a first date so you can (hopefully) enjoy getting to know someone new.
Making conversation on a first date can feel like a delicate balance between getting to know each other and keeping things light and engaging. You want to ask questions to get to know them and see if there’s a connection , but may not want to get too personal too soon… It can be tricky!
And while we all hope to have a great conversation that flows naturally, sometimes you run out of things to talk about and you hit an awkward pause. We’ve all been there.
Having a few extra questions in your back pocket can be a life-saver in these moments and you might even keep you from feeling panicked or self-conscious when the conversation hits a natural lull.
Why asking questions on a first date is important
Asking questions on a first date is a chance to really get to know the person you’re with. And when you ask thoughtful questions, it can help ease some of those nerves and bring a more natural, flowing conversation.
The right questions can give you a way to learn about their hobbies, values, and what makes them tick. Plus, it helps you discover what you might have in common.
Being curious without being too serious, or showing interest without being nosey is key. Everyone likes to feel heard, and being genuinely interested in your date’s answers can make them feel valued and comfortable.
By the end of the date, hopefully you’ll both feel like you learned something new about each other and had a good time doing it.
How to have a fun and engaging first date
You might feel pressured to make a great first impression on a date—it’d be weird if you didn’t— but what matters most is making the date enjoyable and comfortable. You don’t need to come off as a person who has no flaws, you’re a human after all.
Try to keep the conversation light, especially at the beginning. Mix in fun and personal questions, but avoid anything too intense. People tend to open up more when they’re in a relaxed environment, so pay attention to how your date responds — if they come alive at a particular topic, dive deeper!
Other helpful guidelines to keep in mind:
Keep it positive: Avoid controversial or overly sensitive subjects.
Be curious, but don’t interrogate: Ask follow-up questions to show interest without your date feeling grilled.
Share about yourself too: The best convos are two-way. While you want to ask good questions you want to make sure that you’re prepared to open up about yourself too.
Be aware of your body language: Lean in slightly to show you’re engaged, and give eye contact.
Stay open-minded: Sometimes the best connections happen when you’re open to new experiences and perspectives. Even if the date doesn’t end in fireworks, a good conversation can make the evening worthwhile.
And if you’re still feeling anxious before a first date, check out these 10 ways to calm first date nerves.
30 questions to get to know someone on a first date
Asking the right questions on a first date can make a date fun and help you connect. The truth is that dating is a process of elimination, and you could meet dozens of people in the world before you find your person.
Dating takes time and if you value your time, you’ll probably want to spend it wisely. If your dates are fun and relaxing, as opposed to stressful and anxiety-inducing, you’ll feel like it was time well spent, even if it’s not a match. When in doubt, think about the kind of questions you’d ask a new friend, it might take the pressure off.
From light and fun to deep and meaningful, here are 30 questions you can turn to the next time you go on a first date.
Fun first date questions
Fun questions can get the conversation started and keep things light. These are the kinds of questions that spark laughter, surprise, or a smile, helping both of you feel more at ease.
If you could travel anywhere in the world, where would you go?
What’s the most random fact you know?
What’s the most spontaneous thing you’ve ever done?
If you could only eat one food for the rest of your life, what would it be?
What have you always wanted to try, but haven’t yet?
What’s the best concert or live event you’ve ever been to?
What’s the weirdest thing you believed as a kid?
Where was your favorite holiday and why?
If you could switch jobs with anyone for a day, what would you do?
If you could live in any time period, which would you choose?
💙 Practice Listening mindfully with our Relationship with Others series. This can help you fully engage in conversation.
Questions for deep conversation
Once the conversation is flowing, you might want to learn more about your date’s values, passions, and the things that matter most to them. This is especially important if you’re looking to date someone who’s values and morals align with yours.
What are you really passionate about?
What’s the best advice you’ve ever received?
What cause or issue is really important to you?
How do you handle stress or difficult situations?
What’s one goal you have for next year?
What skill do you wish you could instantly learn?
If you could swap lives with anyone for a day, who would it be?
Do you believe in luck, or do you think we make our own?
What’s the most interesting place you’ve visited?
What’s your favorite childhood memory?
💙 Explore how asking thoughtful questions can lead to Deeper Communication in this session from the Daily Jay.
Questions to get you out of awkward silence
Even with the best intentions, sometimes a conversation might hit a lull. It’s completely normal! A well-timed quirky question can pull you both out of any awkward silence and get things moving again.
What’s the weirdest food combination you’ve ever tried?
If you had to be in a reality TV show, which one would it be?
What’s a silly fear you have that not many people know about?
What are your hidden talents?
What’s the last show you binge-watched, and why did you love it?
How do you love to spend a weekend?
What’s the most embarrassing thing that’s ever happened to you?
What’s your favorite book or podcast?
Do you prefer the mountains or the beach?
If you could have any superpower, what would it be?
How to stay safe on a first date
While first dates are exciting, it's important to prioritize your safety. Meeting someone new—especially if it’s through an app or a blind date—requires a bit of extra caution. Take a few simple steps to protect yourself so you can have a fun, safe experience.
Meet in public places: Choose a busy, well-lit location like a café or restaurant for your first date.
Let someone know your plans: Share details with a friend or family member, including who you're meeting, where you’re going, and when you expect to finish.
Trust your instincts: If something feels off, it’s okay to leave the date early. Your safety is the priority.
Avoid oversharing: Keep personal details like your home address or work specifics private until you feel comfortable.
Drink responsibly: If alcohol is involved, pace yourself to stay in control and aware of your surroundings.
Have your own transportation: Plan how you’ll get home, so you don’t rely on your date for a ride.
First date questions FAQs
What questions should I ask on a first date?
On a first date, start with questions that are light and fun. These can help break the ice and set a relaxed tone for the evening. Asking about favorite travel destinations or what someone likes to do outside work can open up the conversation naturally.
As the date progresses, you can move to more thoughtful questions, like asking what they’re passionate about or what their goals are for the next year. These questions allow you to learn more about their interests and values without diving too deep too soon.
Mix playful questions with more meaningful ones, and balance the conversation by sharing about yourself, too.
How can I use body language to improve engagement on a first date?
Simple things like leaning in slightly when your date is speaking, nodding to show you’re listening, and maintaining eye contact can make the other person feel more valued and heard. Smiling is also important—it shows you’re enjoying the conversation.
Try to keep your posture relaxed and open. Crossing your arms or looking away too often can come off as disinterested, even if that’s not how you feel. A few subtle gestures can go a long way in creating a warm atmosphere, where you both feel more connected and at ease.
If you want to learn more, here is how to read body language for better emotional awareness.
How can I avoid awkward silence on a first date?
If the conversation lulls, try asking a quirky or fun question to bring the energy back. Something like, “What’s the weirdest food combo you’ve ever tried?” can spark a lighthearted discussion and ease the tension.
You could also comment on something around you—like the music playing or the vibe of the cafe you're in—to keep the conversation moving.
Don’t be afraid of a little quiet time, though — sometimes it’s okay to take a breath before jumping into the next topic. If the conversation flows naturally most of the time, a short pause here and there won’t make or break the date.
What are some red flags to watch out for during a first date conversation?
While first dates are about having fun and getting to know someone, there are a few red flags to keep in mind. These behaviors may hint at deeper issues, so trust your gut if something feels off.
If your date dominates the conversation, cuts you off frequently, or seems uninterested in what you’re saying, it can be a sign they’re not as considerate or respectful as you’d hope.
If they’re too invasive with personal questions early on, or if they bring up topics that make you feel uncomfortable.
If they talk negatively about past relationships or other people right from the start.
If they steer the conversation towards sex or intimacy too soon.
If they make you feel like the date is transactional.
How do I know if my first date questions are too personal or invasive?
It’s natural to want to dive deep and get to know someone on a first date, but it’s important to gauge how comfortable your date is with the conversation. If they seem hesitant to answer, give very short responses, or try to change the subject, that question may be too personal for a first meeting.
Pay attention to their body language — if they look uncomfortable , switch to a lighter topic and give them space to share as much or little as they’d like.
If the conversation is flowing well, you can gradually move into more meaningful discussions (here are 30 questions that can help you get to know someone deeper). But always respect their boundaries and comfort level.
What should I do if the conversation on a first date feels one-sided?
If you feel like you’re doing all the talking on a first date, pause and encourage your date to share more. Ask open-ended questions, like “What do you enjoy doing in your free time?” or “Tell me about something you really care about.” This invites your date to open up and take a more active role in the conversation.
If they still don’t engage much, try giving them some space by pausing to allow them more time to respond. Sometimes, nerves can make people a little quieter, so being patient and offering a few follow-up questions can help.
But, if the conversation feels one-sided throughout the entire date, it’s okay to acknowledge that it might just not be the right fit. You can always politely exit a date early if you feel like it’s not a good use of your time.
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