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7 Thought-Provoking Questions to Ask on a First Date (That Go Beyond Surface Level)

When you imagine a first date with someone, do you cringe with anxiety or smile with hopeful optimism?

Your answer will likely depend on your past experiences with first dates. When you agree to meet up with a potential romantic interest for a first date, it’s natural to feel a certain amount of anxiety. Meeting someone new is scary! Not only do you want this individual to think you’re the coolest person around, but you likely also feel anxious about whether or not you will like this person. There’s only so much you can gather about a person’s personality from their online presence, so it’s only natural to anticipate a real-life meet-up with someone and hope for the best.

This first date can be hard to get through, however, even if your love is written in the stars. Some people may be more adept at keeping the conversation flowing, while others may struggle to find a topic to discuss due to the anxiety they feel. That’s why it’s important to be prepared ahead of time. You wouldn’t walk into a big test without studying and preparing the night before, so why wouldn’t you do the same for a first date? In this article, we provide seven thought-provoking and insightful questions to ask on a first date that are sure to keep the conversation flowing as well as go beyond the surface level and allow you to really connect with your date. 

You wouldn’t walk into a big test without studying and preparing the night before, so why wouldn’t you do the same for a first date?

Avoid Everything You’ve Heard Before

There’s nothing more disappointing than sitting down for a first date and all the other party asks are surface-level questions like What’s your favorite color? Your date has answered this question so many times — primarily in middle school — that the conversation is doomed to a dead end after the inevitable answer of turquoise or forest-green. The same goes for similar questions like What’s your favorite animal? How much can you really learn about someone by finding out that they love river otters? 

For the sake of your date and the direction of your potential future together, avoid these cookie-cutter questions. It can be beneficial to engage in a bit of role-playing as preparation for the first date. Imagine yourself in your date’s shoes — what would you want to be asked about? The goal of these questions is to go beyond mindless, surface-level conversation and really dive deep into what kind of person your date is. Ideally, you want to leave this first date with a solid understanding of who this person is and whether or not you want to see them again. 

Don’t get it twisted: physical attraction and chemistry are definitely important in a potential partner, but being able to maintain a comfortable conversation and genuinely liking the fundamental human being underneath their physical appearance is by far the most important thing. We are assuming you’re already attracted to this person, so these questions are not meant to make you fall in love with someone you don’t even enjoy looking at or get along with. Rather, they’re meant to give you a better understanding of the person you’re already interested in pursuing as well as aid you in keeping the conversation from going stagnant.

1. What’s Your Favorite Quality About Yourself?

When you really want to get to know someone, this is a great question to start out with. Make sure you have an answer to this as well, as your date may turn the question around on you after they’ve answered. When you ask someone to describe their favorite quality about themselves, not only is your date going to talk positively about their qualities, but they may appreciate the sincerity of the question as well. 

If this catches your date off-guard and they don’t have a response immediately, pay them a compliment! Don’t overplay your hand, but if they can’t give you an answer as to what their favorite quality about themselves is, tell them what your favorite quality about them is. Yes, you just met this person face-to-face, but something like, “Your smile is so bright it lights up the room, so that would be my favorite quality about you so far,” can really go a long way. Keep it short and sweet, however. You want to make your date feel more comfortable, not like you’re in love with them as soon as you sit down. 

2. If You Could Work Any Job and Not Worry About Money, What Would You Do?

Answer this question for yourself before your date. Would you write novels in a cabin in the mountains and live out your days in seclusion and solitude? Would you be a lifestyle photographer for athletes or celebrities and live in a high-rise in Manhattan? Whatever your ideal job looks like, it’s important to share at least some common ground with your date on this question.

We all have dreams and ambitions, and almost everyone has an answer to this question, even if they’ve never thought about it before. This is a great question because it will show you if your interests and goals line up with one another. If they don’t line up at all with each other, it’s better you find that out on the first date rather than farther down the road. Additionally, this question might lead the conversation to a fun topic that can reveal a lot about your date.

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Bonus Question: If You Won the Lottery Tomorrow, What Would You Spend the Money on First?

Granted, money isn’t everything, and there are more important things to talk about than winning the lottery. However, a person’s answer to this question can tell you a lot about their priorities. If you had so much money that you were free of financial stress, what would your life look like? Extravagant parties and expensive gifts? A house in the country with plenty of acreage? You’re more than likely going to have different answers to this question, but it’s still fun to learn how your date would handle sudden and immense wealth. 

3. How Would You Describe Your Closest Friends?

It can be beneficial to take the spotlight off of your date for a moment and ask them to describe what their best friends are like. Take note of how they talk about them because it can show you a lot about how they view friendship and what they value in companionship. If they speak negatively about their closest friends, that may be cause for concern, so long as it’s not done in an obviously sarcastic or joking manner. Everyone loves to give their friends a hard time, but it should be obvious that you care about them and value their presence in your life.

4. Are You the Type of Person to Tell Someone If They Have Food Stuck in Their Teeth?

This one is sure to catch your date off-guard and will likely get you both laughing. Not only will this keep the conversation moving along, but it will provide further insight into the type of partner your date is. Though this is technically a yes or no question, there’s not really a right or wrong answer. Whether someone would or wouldn’t divulge the information that there’s a piece of spinach stuck in your teeth doesn’t exactly change anything about their personality or viability as a potential partner, but it does give you insight into how they might communicate. 

You might have preferences on how you want a partner to go about such a situation. If you forgot to apply deodorant and don’t smell particularly pleasant, do you want your partner to let you know? Or would that embarrass you, and you’d prefer not to be told? Whatever your preference, this question will hopefully tell you whether you and your date would be successful at communicating. 

5. Would You Rather…?

“Would you rather” questions are an excellent go-to for their ability to break the ice and for the endless possibilities that these questions provide for conversation. You can be as whimsical or as deep as you want to be. For example, you could ask, “Would you rather spend a week at the beach or sight-seeing in Chicago?” or something much deeper, like “Would you rather marry someone you’re in love with and struggle financially forever, or marry for money and never truly fall in love?”

Let the nature of the conversation steer you in a direction that suits the context of your date. Don’t throw out an intense “would you rather” question if the conversation has been primarily light and fun, and don’t ask if they’d rather have noodles for arms or hot dogs for fingers if they’ve just shared something intimate about their closest friendships. Let the context of your date guide you!

6. If You Had a Time Machine, What’s the One Moment You’d Return To and Do Differently?

Oh, how different each of our lives would look if we had the ability to turn back the clock. Though your date may not have an answer at the ready, you’d be hard-pressed to find anyone who wouldn’t go back in time and change something. This question can be a good indicator of what your potential partner regrets in their life and what they would do differently, which can tell you a lot about a person. Asking yourself this question can be a real eye-opener as well.

Would you go back in time right before a Superbowl and win a massive sum of money? Would you return to your first day of college and lay the foundation for pursuing an entirely different career? You may not even realize it at first, but your answer to this question will really show you what your priorities are in life. 

If your main objective is to ensure you will be financially secure in life, try to dive a bit deeper. There’s nothing wrong with wanting to be free of financial stress, but you should really dig deep and find a moment that altered the trajectory of your life forever and ponder how things might have been different had you taken another path.

7. What’s Your Least Favorite Quality About Yourself?

It’s important to connect with your date and show a little bit of vulnerability. Answer this question yourself first to make your date feel more comfortable, but don’t overburden them with something heavy. Stick with something that’s true but also easily relatable. For example, you could say something like, “My least favorite quality about myself is that I can sometimes take myself too seriously, and I’m trying to work on that.” This will not only show that you’re trying to better yourself, but it will encourage your date to open up to you about something they want to change about themselves as well.

This is a great question for the end of your date because it will allow you both to connect through your vulnerability. Everyone has personal qualities they can improve, and finishing the date with this question will open the door to talk about deeper things on your second date. 

Dive Beyond the Surface

First dates are scary for everyone, even if they’re exciting too. When you like someone and want to pursue a relationship with them, you naturally want to present your best qualities and see the best in the other person. There’s no way to really get to know someone just by asking mindless questions about their favorite food. Things like that are bound to come up naturally in conversation as the relationship progresses. That’s why it’s important to focus on deeper questions like the ones in this article to get to the bottom of what makes your date unique.

Always remember: You know yourself better than anyone. If you are ever in a situation where you just don’t get along with someone or feel at all unsafe, remove yourself from the situation as calmly as possible. Always listen to your instincts and do what’s best for you. You’ll know when you’ve found someone who’s worth the sweaty palms and butterflies, and when you do, you’ll have a handful of thoughtful questions at the ready!

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