There’s always a kind of apprehension when it comes to first dates. Will you like each other? Are you going to be a good match? Will it work out? Or are you doomed for relationship failure? No doubt, thinking about the countless ways that your first date could go can make you feel scared and cautious.
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But while those feelings are absolutely normal, there’s a lot to gain out of being level headed. For instance, making it a point to use your first date the right way will help you learn more about this new person in your life so you can get a deeper understanding of who they are. Asking the right questions on your first date can help you work out the kind of future you’ll have with this specific person.
So, what kind of questions should you ask? What information matters? Find out what first date questions you should never forget to ask, and make the most out of that first encounter to benefit both you and your special someone.
Family History and Background
Sure, it might sound boring to ask about your date’s family but learning more about their roots, where they came from, and how they grew up can give you a better understanding of their true personality and character. A person’s family history will play a big role in shaping the kind of adult they become, so some of the best first date questions to ask should revolve around their family and background.
Here are a few first date questions you can start with:
- How many siblings do you have?
- Where did you grow up?
- What were some of your favorite things growing up?
- What’s your favorite childhood memory and why?
- Did you have any pets when you were little? What were their names and what was it like to have them?
- What’s the scariest thing you ever encountered as a kid?
- What school did you go to?
- Do you have any childhood friends that ended up being lifelong friends? Who were they and what are they like?
- What were your parents like when you were growing up?
- What was your family’s favorite thing to do on weekends?
The point of asking about your date’s childhood is to learn more about the way they interact and connect with the people who are closest to them. Secure family ties might mean that your date values loyalty, quality time, and meaningful relationships. Of course, there’s never a guarantee as your date might only be showing you what they want to show, but it’s never bad to start learning more about their history.
Employment and Nature of Work
Again, these might not seem like the most exciting questions to ask on a first date, but they will shed light on the kind of person you’re face to face with. Learning more about someone’s work will tell you what they’re interested in and the kind of work ethic they bring to the table. In most cases, learning about their work may also help you map out the kind of relationship you might have with the person you’re on a date with. For instance, busy work schedules and demanding jobs with mean bosses can mean limited time for you and your special someone to bond and go on dates.
Here are some work-related questions you might want to ask:
- Where do you work and how long have you been working with them?
- Can you describe your usual work day?
- If there’s one thing you can change about the nature of your job, what would it be and why?
- What’s your favorite thing about the work that you do?
- Are you the early bird or are you typically the last one in?
- What do you like about your boss? What do you dislike about them?
- What do you like to do for fun after a busy work day?
- Who are your work friends? What do you like about them?
- If you could have things your way, where would you be in terms of your job 10 years from now?
Discovering more about their work and employment will help you figure out their unique goals and aspirations, and how they hustle to reach those desires. If you detect that your date might be the lazy, come-what-may type of person, it can spell trouble for your future relationship especially if you’re looking for someone who can be a little more dedicated to building a stable family life with you.
Hobbies and Interests
What a person does in their spare time will clearly depict the things that are most important to them. Especially these days when most of us don’t have a lot of time to spare, finding out what your date likes to do when they’re not busy with work should help you discover more about the things that they think are worth spending their limited time on.
- If you could have an entire day to yourself, what would you do?
- If you could take the whole month off, how would you spend your time?
- What do you like to do for fun?
- What are the weekends like for you?
- Are there any advocacies or groups that you’re a part of? What are they?
- What’s one thing you wish you could spend more time doing?
- If you could take up a new hobby, what would it be and why?
- What one talent do you wish you could have?
- If you could become a master of something, what would that something be and why?
Learning more about your date’s interests and hobbies won’t only help you understand what they find important, but will also help you figure out whether you’d enjoy the time you spend together. Finding common ground in the things that you both like and do can make it easier for you to establish harmony in your relationship. If you feel that you don’t have too much in common, think about whether or not you’d be willing and happy to take up one of their hobbies or interests to establish common ground.
Plans for the Future
Let’s face it – the main reason why many of us go out in search of a romantic interest is because we’re on the hunt for a partner we can spend the rest of our lives with. Sure, it might be hard to tell if the person sitting in front of you would be a viable life partner since you’re only just on your first date. But asking the right questions can make it easier for you to understand whether you’d be on the same page if your relationship does end up flourishing.
- Where do you see yourself living 10 years from now?
- Do you think you’d be the kind of person who would be happy to settle down or is that something that doesn’t fully appeal to you?
- How do you envision yourself spending your senior years?
- Kids – yes or no? How many children do you think you’d want to have when you’re ready?
When asking about future plans, it’s best to keep it casual. Of course, it pays to learn about your date’s goals and aspirations, but try not to get too serious! Questions that make you seem like you’re prying into personal territory might scare your date away. Don’t get too intimate and keep the conversation light. Try to use these questions sparingly and ask them only when appropriate.
This or That?
Aside from helping you learn more about your date in terms of their preferences, this or that questions can be fun topics to talk about. If you find that you disagree on certain answers, these can also become the beginning of fun, friendly debates to keep your evening interesting. Remember, it pays to come prepared with a few interesting questions to ask on a date just so your special someone doesn’t feel like you’re putting them on the spot.
- A one-month cruise to a tropical destination or a long vacation in the Alps?
- Coffee or tea?
- Breakfast or dinner?
- Read a book indoors or spend aa night out with friends?
- Wine and dine or Netflix and chill?
- Comfy casual or fashionable and formal?
- Dress shoes or comfy sneakers?
- Sports or lounging?
- A trip to the gym or a trip to a new restaurant?
- Japanese food or Italian?
- Morning or night?
- Cats or dogs?
- Rain or sun?
- Go on a hike or go bar hopping?
- Outdoors or indoors?
- Movies or TV shows?
If you’re going down the this-or-that lane, make sure you’re not putting sensitive topics on the table. Questions that dwell on political and religious views don’t always do well as first date questions. So be careful about your chosen topics and always keep in mind that you’re trying to maintain a light atmosphere whenever you ask your date to learn more about them.
These first date questions don’t only let you learn more about your special someone, but they also just keep the date interesting. After all, the last thing you’d want would be to end up on a dry night out that leaves both of you wanting to call it an evening and never see each other again. Making your effort to keep the conversation going will help make the night more enjoyable for both of you, and may even increase the chances of a second date. So here are some interesting questions to ask on a date.
- What’s one vacation trip that you’ll never forget? What was it about the experience that makes it unforgettable?
- When’s the last time you did something for the first time? What was it and how did you feel about it?
- When you’re feeling shy and uncertain, what do you usually do?
- How did you meet your best friend and why do you think your relationship has worked out so well?
- Did you ever have to cut someone out of your life? What happened, if you don’t mind sharing?
- If you could live anywhere in the world, where would you move and why?
- What are you looking for in a partner? Do you have any clue as to why your previous relationships didn’t work out?
- What’s the most expensive thing you’ve ever bought for yourself?
- What’s one piece of important advice that you think everyone should know?
- What’s your favorite place in the whole world and why?
- Describe your perfect day.
- What accomplishments are you really proud of?
- If you had all the money in the world, what would be the first three things you’d buy and why?
- If you won the lottery, name 10 things you would spend your new funds on.
- What’s the worst experience you’ve ever had on a date?
- What is your go-to movie or TV show if you just can’t find anything else that you’d like to watch?
- What are some of the little things that make you smile or that brighten your day?
- If you could tell your 10 year old self one thing, what would it be and why?
- What kind of music do you like to listen to?
- What’s your favorite memory of your childhood?
- What do you like to do over the holidays?
- What do you think the world will look like 50 years from now?
The nervous feeling in your tummy might make you want to clam up during a date, but don’t let it get the best of you! Get the conversation started, keep it flowing, and give your date an evening to remember by coming prepared with the right questions to ask on a date. Make a mental note of these suggestions, keep it casual, and try not to be too mechanical about your questions!
Remember, your objective is to learn about your date. It doesn’t matter how many questions you manage to ask, but how meaningful your conversation becomes as the date draws on. And who knows, you just might spark enough interest to call for a second date.
Susan majored in English with a double minor in Humanities and Business at Arizona State University and earned a Master’s degree in Educational Administration from Liberty University. She taught grades four through twelve in both public and private schools. Subjects included English, U.S. and world history and geography, math, earth and physical science, Bible, information technologies, and creative writing.
Susan has been freelance writing for over ten years, during which time she has written and edited books, newspaper articles, biographies, book reviews, guidelines, neighborhood descriptions for realtors, Power Point presentations, resumes, and numerous other projects.