Beyond the Surface
By date three, hopefully you have relaxed past being nervous into pleasantly buzzed with curiosity. By this point you have also most likely discussed the basics such as where they were raised and what they do for a living. So with that in mind, here are 20 in-depth questions perfect for the third date vibes.
1. What’s your biggest "unpopular opinion"?
"Do you think pineapple on pizza is wrong? Or secretly despise a movie everyone loves?" This is their opportunity to express how they deal with being different. You want to know if they can hold their own convictions with some levity. They'll show you their weirder side while remaining casual.
2. How do you usually spend your time when you're completely alone?
Everyone recharges differently. Some people love curling up with a book for hours and hours; others prefer heading into the woods for a weekend alone. Asking this question is a subtle way of determining how much space your partner needs.
3. Is there a specific goal you’re working toward?
Outside of work and careers, everyone has something that they’re working toward. It could be a painting they’ve been perfecting or training for a 5K (without their boss telling them they have to). Most people love talking about something that they’re good at that they don’t do for a living.
4. Which childhood memory always manages to make you smile no matter what?
This question can get heavy, but asking for their favorite memory specifically will prompt a lighter response. Not only will you learn about their past and what they cherish about it, but you’ll learn who played the biggest roles in their life.
5. What’s the most adventurous thing you’ve ever done on a whim?
Spontaneity is a great trait to gauge early on to see if your lifestyles will actually align. Whether it's telling you about deciding to road trip at the last minute or trying weird food on a whim, you learn about how adventurous they are. You can follow up with your own afterwards to keep the conversation going.
6. Do you consider yourself a person who lives to work or works to live?
Asking about someone’s work life gives you insight on where a significant other would slot into their life. Some people live and breath their jobs. Some people work to support their passions. Knowing how they view work is crucial to your future together.
7. What is your absolute biggest pet peeve when you're out in public?
This question is great because we all have our small little things that annoy us. Someone takes forever to decide what they want? Boom, pet peeve. Talking loudly on their phone? Double boom. You’ll either be able to pet peeve together or you’ll know that you’re the annoying person
8. If you could live in any other city for just one year, where would you go?
This question is great for figuring out what someone’s travel desires are. It also lets you know what type of atmosphere they enjoy. Will you live together there? No. But it helps you know what they find interesting about the world. Maybe you’re both into Japanese culture or both want to live by the beach.
9. What was the last thing that made you laugh until you actually cried?
Every couple seems to have that make or break quality when it comes to humor. Do you and your date find the same things funny? By asking this question you’ll know if you’ll be able to keep each other entertained during those awkward silences. If you can make each other laugh, you’re on your way to winning them over.
10. How do you typically handle it when things don't go according to your plan?
Life is unpredictable. Learning how someone handles when life throws them a curve ball is incredibly revealing. Not to mention, it’s not super forward in asking about their emotional stability.
11. What’s a skill you’ve always wanted to learn but haven't started yet?
A question about the things they’ve always wanted to learn reveals their secret passions and inner fascinations about the world. Do they want to learn how to play the cello? Are they interested in learning how to code? Either way, they haven’t given up on having dreams. It also plants the perfect seed if you’re looking for fun date ideas for a second date.
12. Who is the one person in your life you can always count on for honest advice?
The people they keep around can tell you a lot about their character and what qualities they value in friends. When they tell you about their “person”, you’ll get an idea of what their support system is like. Who knows, you may even become their “person” one day if they think you’re worthy of deep, meaningful relationships.
Priscilla Du Preez 🇨🇦 on Unsplash
13. What does a perfect Sunday morning look like in your ideal world?
Some like to sleep in. Others are up at the crack of dawn to grab some farmers market coffee. Life is about syncing your bodies with the people you love. That’s why it’s important to know if you and your Sunday morning rhythms align. Ask them this question to learn more about their daily life without being too nosey.
14. Is there a book or movie that completely changed the way you think?
We all know each other by now. No more boring questions that you could ask just about anybody. This question forces them to open up about the thoughts and ideas that matter to them. Listen closely and you’ll pick up on their innermost values and what themes resonate with them.
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15. What’s the best piece of advice you’ve ever received from a stranger?
Sometimes the most profound wisdom comes from the most unexpected places. ee how perceptive they are to the world by asking them this question. This always sparks an interesting story that you’d never hear on a first date.
16. How would your closest friends describe your role in the group?
The “mom” of the group? The clown? The quiet listener everyone runs to when things get too crazy? Figuring out how they view themselves in their friend group can help you predict how they’ll act around you.
Jonathan J. Castellon on Unsplash
17. What’s one thing you’re incredibly proud of that you don't get to talk about often?
Letting someone boast about themselves is a wonderful way to make them feel proud and heard. We tend to hide our best qualities and accomplishments so we don’t come across as arrogant, but the third date is the perfect time to unleash them! You can learn what they value about themselves by their answer.
18. Do you prefer to plan every detail of a trip or just see where the day takes you?
This question allows you to peek into their inner need for control or if they thrive on being a free spirit when in unknown situations. Traveling is a huge part of any relationship, so it’s good to know how your partner likes to do things before you book a flight. Who knows? You might even pick a destination for your next trip.
19. What’s the most significant thing you’ve learned about yourself in the last year?
We are all constantly growing as people, and someone who spends time thinking about their life is a keeper. This question not only tells you they care about self-betterment, but it shows you that they are comfortable with the concept of time passing. Bonus points if it leads to a deep and meaningful conversation.
Priscilla Du Preez 🇨🇦 on Unsplash
20. What is the one thing you’re most looking forward to in the coming months?
Ending your date with a question that makes them think about the future is a great way to leave your date wanting more. If they say a concert, you can hint that you have tickets. If they say a job promotion, you can celebrate with them if things work out. If they say summer, you know you have a fun date coming up at the beach.
