10 Simple Questions to Help You Learn Everything You Need on a First Date

First dates can be exciting and awesome, but they can also be nerve-wracking, awkward, and a real pain. They are sort of mini-interviews disguised as social outings, whether we like to admit it or not. That’s why figuring out what to talk about ahead of time with a list of good first date questions and conversation starters are essential.

A good first date can be many things. It can be memorable, dramatic, or hilarious. Ultimately though, a good first date is illuminating, giving you a clearer picture of who your potential partner is. However, with social division affecting almost every aspect of life, it can be hard picking out conflict-free and illuminating questions. That is why we have compiled these questions to help pave the way to your next relationship.

Revealing Questions You Should Ask on a First Date

Before you start learning, keep in mind these questions are not to be rolled out like you are reading from a questionnaire. They are conversation starters, a way to open the many doors into your date’s personality and character.

The world is a complicated place, and the idea that a person’s political opinions tell you everything you need to know about them is not as straightforward as you might think. Using these questions, you can peel back the nuances, revealing who they really are.

Another tip is to rephrase these questions. Remember, you are not the only one on the internet looking to make sense of an increasingly convoluted dating scene. Pick out the point of the questions and present them in your own way. It will show you are creative and good on your feet. With that settled, here are ten questions to make your next date worthwhile.

1. What Does A Regular Day in Your World Look Like?

first date questions
image source

A great thing about this question is how it collapses all the commonplace questions of a regular first date into one interesting question. ‘How was your day?’ ‘What do you do?’ ‘Did you have a good day?’ and other variants can be nice, but they are boring. There is also the added fact that they might not give a detailed answer.

With this question, you cut through the blandness and get into something far more fascinating.

Unless your date is a terrible conversationalist, you will most likely walk away learning a lot more about them and their life. It also has the added benefit of freshening up their perspective if they had a bad day before your date, making them appreciate the regular days more.

2. Do You Have A Passion Project?

If the first question goes well, this is a great question to transition to on a first date. With a clearer picture of their professional life (if there is one), your date gets to dive into what they would rather spend their days doing or what they really want to work on.

Now, this is where it gets interesting. Because you now know what their regular day looks like, you are in a better position to make insightful comments on how they can pursue or achieve their project without getting the age-old ‘I don’t have time for that.’ Plus, it puts you far away from the overused ‘what are your hobbies?” question.

3. Where Is Your Happy Place?

We all have a happy place, and if you don’t, you should probably find one. As the name suggests, they help rejuvenate our minds and improve the quality of our lives, emotionally at least. But diving into the science of happy places on a first date is way too serious. So how do you do ask?

Framing the question like this helps because you will get to learn more about their preferences. Suppose you have an in-depth understanding of the psychology behind happy places. In that case, you can also learn things like their core personality and mental state. Else, it can just be a fun way to learn how to care for them if your date ever leads to something serious.

4. What Are Your Pet Peeves?

There is a conflict when it comes to how people primarily see first dates. Some see it as screening out bad eggs, while others see it as an adventurous experience. This divide often informs the kind of questions that dominate the conversation, with those in the first group often preferring negative or conflict-inducing questions. But it doesn’t have to be that.

There are still ways to learn about your compatibility without wearing your differences on your sleeve.

Asking about their pet peeves is one of them. The answers are typically simple low-consequence issues that fit into the lighthearted nature of a first date. You will learn about something they find significant and determine if you fit into the picture without necessarily getting into a conflict.

5. Do You Have Something You Wish You Were Better At?

We all have insecurities. For some, it is crippling, and for others, it is fuel. But we all do. Still, pointedly asking if your date has insecurities could spark conflict or make them retreat into their shell. However, asking if they have something they wish they were better at or in a similar way throws a casual spin on the subject, eliminating its inherent toxicity.

Furthermore, it helps you avoid the well-trodden path of ‘What are your hopes and dreams?’ If you do it right and your date is open enough, it can spark a bonding moment between the two of you, ultimately increasing your chance of a second or third date.

6. What Is the Favourite Gift You’ve Ever Received?

first date questions
image source

Gift-giving is one of the basic social etiquettes that seem to mean nothing on a deeper level but actually do. Research shows a bad gift can hurt a relationship, proving gifts have a profound effect on us. If you are trying to learn more about your date on the first date, asking questions about their favourite gift is a great way to do so.

Not only is it an uncommon question, but their answer will reveal what matters to them. You are not supposed to blurt it out of the blue, though. You should pick your moment, like when someone is celebrating their birthday in your vicinity.

7. Who Were You as A Kid?

How many times has someone asked you to ‘tell them about yourself’ or ‘Are you close to your family?’ The first can be exhausting, and the second can be too invasive, especially for a first date. Asking what they were like as a kid, though, keeps things light.

It gives the air of reminiscence and laughing over the foolishness of childhood years. Even if they fail to provide an in-depth answer, you are still more likely to get a blurry picture of their younger years. Moreover, if you are conversant with Birth Order personality types, it can also be a way to shed light on their personality.

8. Seen Any Good Movies or TV Shows Lately?

You probably use this already as a casual question, but it can be a way to learn more about your date. Most people stick to the surface ideas like whether a show or movie is good or an actor is great. But asking why they prefer one genre over the other and why they think a show or movie had a bad ending can be a great and relaxed way to learn more about your date and how they think.

You can also ask about which fictional character they relate to the most. It may seem childish, but once you realize first date questions should be easy and fun, then you will see the appeal and effectiveness.

9.    What Foods Are Off the Table for You?

How many times have you started a conversation on one silly topic, and you end up discussing something with import? Believe it or not, food is one of the best triggers for that. Asking about the kind of food your date won’t eat can lead to conversations about allergies, bad date experiences, or PTSD if you ask the right follow up questions.

Obviously, the goal is not to reveal their hidden struggles but rather to show how simple questions can help make your first date more meaningful and engaging. One thing, though, do not push if they are not forthcoming with more in-depth answers.

10.  What Is A Random Fun Fact About You?

Lastly, everyone has something interesting about them that makes them stand out in their environment while not necessarily unique. You can find it with a question like this and bond over your weirdness. If neither of you is weird, you can spin the question into a random fact about what they find strange in others.

It will give you both something to laugh at or lightly debate over. Also, because it is not a question that comes up in regular conversations, you are likely to learn something very few people know about them, which can be very bonding.

There are more questions, but by now, I am sure you get the idea. Avoid bland questions on your first date and explore simple and exciting ideas that connect to their deeper personality and interests. Overall, just remember, regardless of the larger purpose, both of you want a good time, and these questions can help you achieve that.

The 5 Questions You Should Rather Not Ask on a First Date

first date questions
image source

It is not just enough to know what to ask but is also necessary to know what not to. As mentioned earlier, the widening divide in the world means many potentially great relationships die before they begin over the wrong term or a poorly phrased question.

There are also a few faux pas questions to avoid on a first date for the socially awkward. Questions that might seem fair on the surface but speak to deeper insecurities or struggles. Plus, it is the first date. The goal is to keep things relaxed and try having a good time with someone new.

Decades of dating experiences have shown there are many questions you should avoid on a first date. Here are five of the most typical questions you should avoid.

1. Would You Tell Me if You are Crazy?

It might be cute, and if it were a second or third date, it would probably be fine. But for a first date, questions that put them on the spot like that can be off-putting. It can also be accusatory, and that is a feeling you definitely don’t want to elicit on a first date.

More significantly, you might be inadvertently communicating that you have met crazy people. It can lead your date to wonder why you have been meeting crazy people, leading to a possible false conclusion that you have traits that attract them. Solution? Just avoid the question entirely.

2. Where Do You See Yourself in Five Years?

It doesn’t matter if you are knocking on 30 or 50, and it is even worse when you are in your 20s. Asking where they see themselves in the future on a first date is point blank bad date etiquette. It makes you look desperate and suggests you are not as interested in them as you are in the goal they can help you reach.

Leave questions like this for the fourth or fifth date, when you have established that you like each other. Then, questions about defining your potential relationship and what you want from it will be fair.

3. Am I the Only One You are Seeing?

Or ‘are you having sex with someone else?’ Both are intimate questions that are out of line unless you have established mutual interest before the first date. It is a faux pas that reveals you do not respect personal boundaries. If you ask if they are seeing someone else, it might suggest you are clingy, jealous, and possessive. Not a great opinion for someone to take home from a first date.

If you go with the sex question, you send the message that is what you only care about. Maybe you are asking because you see the date leading to sex and want to be sure they don’t have multiple partners. Rather than ask, just live by the golden rule of using protection by default.

4. Are you Close with Your Parents?

It is the first date, and it is not up to you alone to determine if there will be another one. Asking about your date’s relationship with their parents is too invasive when you could go back to being strangers after that evening. Also, if the answer is anything but good, you have managed to trigger negative emotions in them and ruined the evening.

Remember, first dates should be a fun, comfortable, and relaxing way to pass an evening. You will not figure everything about your potential partner on the first night. So, pace yourself and keep the heavy stuff for much later.

5. What Happened to Your Last Relationship?

Believe it or not, people make this common mistake on the first date, probably because it is intuitive. It exists on the same plane as the parent’s question. If it was a bad breakup or divorce, you have ruined the evening and put their emotions in jeopardy.

Another consequence is if they answer the question, you might find yourself having to compete against their ex. Either because they are so great or so bad, you feel the need to eliminate any similarities to increase your prospect as a partner.

All in all, it is a wrong move for all involved, and if you have a top-five list of questions to avoid on a first date, it should be one of them.

Fact Check: We strive for accuracy and fairness, if you've found a possible error, be it factual, editorial or something that needs updating, please contact us
Adeola Seun
Adeola Seun
An avid writer for over 8 years with a purpose in mind – I express my thoughts so that others can be inspired to leave their dead weights behind, and forge ahead without holding back. Other than writing, I like to also spend my time playing video video games, watching movies, and maintaining a love/hate relationship with Arsenal.

Recommended

Featured Today

Read This Next